If you’re looking for the best way to experience summer on the East Coast, it’s got to be driving the beautiful coast of Maine.
With over 4,000 islands and the most coastline of any state in the United States, road tripping the coast of Maine is a bucket list item if there ever was one!
Taking a Maine coast road trip encompasses everything that is quintessentially New England in summer, from its seafood shacks to its charming coastal towns to its sandy beaches on the pristine Atlantic coast.
This road trip itinerary includes plenty of scenic Maine coastal drives, small towns worthy of day trips, and yes — plenty of beach time!
How This Maine Itinerary Works
This road trip begins in Southern Maine and ends in Northern Maine. It assumes you are within driving distance of Maine and are bringing your own car.
When I did this Maine road trip, I flew to Boston, Massachusetts from San Francisco. My friend came down to meet me in Boston, where we spent two days, and then we drove up to Maine from Boston.
If you do this Maine road trip from Boston, I suggest renting a car in advance from Boston Logan International Airport. They have the best rates and their location is convenient for the city. Compare prices on car rentals here.
From Boston to the first stop on this coastal Maine is only an hour and a half drive, so it’s easy enough to start your trip there.
From the end of this itinerary, you could return your rental car in Bangor (the nearest airport to the final stop, Acadia National Park) or you could drive back to Boston if that’s better on your budget.
One-way rentals are often really pricy, so while this definitely adds time and mileage to your trip, it may be worth it for the cost savings.
The drive directly from Acadia National Park to Boston is about 5 hours with normal traffic, though it may be worse on weekends or holidays.
Where to Stay in Maine
This itinerary is crafted to be customizable to your personal travel style. Depending on how you prefer to road trip, you can adjust it.
I personally hate moving hotels every night, so I crafted this Maine itinerary with this in might, so that wouldn’t be strictly necessary.
However, if you do the itinerary this way, you may have to do a little more driving in between each stop and that may also involve a small amount of backtracking.
Alternately, you could move hotels each night to keep moving without backtracking quite so much.
(No matter what, to some extent some backtracking is unavoidable due to the unconnected peninsulas and islands you’ll visit, particularly in Midcoast Maine.)
Here are two ways you could do it:
| Night | Option 1 (Fewer Stops) | Option 2 (More Stops) |
| 1 | Ogunquit or Kennebunkport | Ogunquit |
| 2 | Ogunquit or Kennebunkport | Kennebunkport |
| 3 | Portland | Portland |
| 4 | Portland | Portland |
| 5 | Brunswick or Bath | Bailey Island |
| 6 | Brunswick or Bath | Damariscotta |
| 7 | Camden | Rockland |
| 8 | Camden | Camden |
| 9 | Bar Harbor | Bar Harbor |
| 10 | Bar Harbor | Bar Harbor |
Your 10 Day Coastal Maine Road Trip Itinerary
Day 1: Ogunquit
Southern Maine is home to some of the few sand beaches along the Maine coast, which tends to trend rockier as it goes further north.
York, Ogunquit, and Kennebunkport are the three most popular beach getaways in Southern Maine – and in this itinerary, we’ll cover the latter two.
These three beach destinations tend to be quite busy with day and weekend trippers from New York, Connecticut, New Hampshire, and Massachusetts, since it’s a relatively short distance from other points in New England.
A general rule of thumb: the further south you are in Maine, the busier it’ll be – with the exception of Acadia National Park, of course.
I didn’t get a chance to visit York on this trip, but I did get to see both Ogunquit and Kennebunkport.
I have to say that I preferred Kennebunkport, but my time in Ogunquit wasn’t ideal as the remnants of a tropical storm were blowing through (which is why I’m using primarily stock & other people’s photography in this section — my photos are really dark and gloomy!)
Drive to Ogunquit.
The first destination on our whistle-stop tour of the Maine coastline is the charming seaside hamlet of Ogunquit.
Frankly, my experience with Ogunquit was subpar, simply for the fact that the remnants of Tropical Storm Fred made there be a total downpour during my stay in the town. It rained to the point of flooding: hardly what you want on a beach getaway!
However, I did get to eat a meal in Ogunquit and browse some of the shops and restaurants, so here is what I recommend you do when in Ogunquit.
Walk the Marginal Way.
First things first: parking in Ogunquit can be a bit of a nightmare. The parking gets worth the further out towards Perkins Cove you drive.
As you drive towards the pier area, there is a very small municipal lot where you can park for $4 per hour… and that’s assuming you can find a spot! We had no such luck, and it wasn’t even a weekend.
More likely, you’ll have to pay $25 for a day pass for private parking. Alternately, you can park in a municipal lot up the road, also at $4 per hour, but then there is a lot of walking. We parked here at Obed’s Lot.
The Marginal Way stretches from the area near Obed’s Lot to Perkins Cove. I suggest parking at Obed’s Lot because it has a lot more space and the walk along Marginal Way along the coast is spectacular!
Admire all the beautiful buildings of Ogunquit on this peaceful coastal walk that passes Little Beach and Israels Head on a one-mile coastal walkway. It takes about 20 minutes to reach Perkins Cove.
Explore the Perkins Cove and Harbor area.
Once you arrive in Perkins Cove — either via Marginal Way or driving directly to Perkins Cove and parking — it’s time to explore the charms of Ogunquit, particularly the harbor area around Perkins Cove. Here are a few shops worth stopping in.
- Whistling Oyster for whimsical and beautiful jewelry inspired by the sea
- Perkins Cove Pottery Shop has gorgeous ceramic pieces for the home — it’s hard not to leave without something
- Blue Whale Trading Company for beautifully curated pieces from local New England artists
Have the first of many seafood meals.
When it comes time for lunch, hit up The Lobster Shack – it has the best reviews of any restaurant in Ogunquit and good prices to boot given what’s on offer.
I didn’t heed my own advice as the Lobster Shack was totally full when we visited and we had to make alternate plans!
It was pouring rain and we couldn’t find parking downtown, so we hopped back in the car and headed to Rose Cove Restaurant. I ordered the fried haddock tacos and they were just OK. Honestly, I wouldn’t go back.
Walk along the Footbridge.
This manually operated drawbridge is one of the biggest draws to Perkins Cove — just look how cute it is!
Take a stroll over the bridge to complete your walk of Perkins Cove and see it from the other side for perspective (and photo opps!).
Spend the day on Ogunquit Beach.
Time for your first of a handful of sandy beaches in Maine! The main (ha) reason why people come to Ogunquit is for its enormous stretch of sandy shoreline… an anomaly in the mostly rocky coastline of Maine.
The powdery sand and gentle waves mean that Ogunquit Beach is a great place for families who are looking for some calm water to wade in and soft sand to luxuriate on.
End the day with another meal.
If you want more seafood, head back to Perkins Cove for one of the other delicious restaurants. Other recommended places in the area include Footbridge Lobster and The Trap.
If you want something different, the Front Porch has a wide variety of sandwiches and entrées for a break from seafood.
Day 2: Kennebunkport
Spend the day on Gooch’s Beach.
I hope you didn’t have too much beach time yesterday… because it’s time for what is, in my opinion, one of the best beaches in Maine!
Gooch’s Beach in Kennebunkport is simply stunning. Lots of sandy coastline means that you can walk nearly a mile on the sand, the cool Atlantic water lapping at your ankles.
Note that the beach is on the narrow side and that during high tide, there can be very little room on the sand for towels! There is more room on the north side of the beach, as this is where the beach is wider.
Another caveat: parking here is rather pricy, at $25 for a day pass for street parking using one of the meters or the Passport app. We found it worth it, but if you are staying in a hotel in the area, you may be able to walk instead.
Parking here at Gooch’s will also allow you free parking access to Middle Beach and Mother’s Beach, as it is all one zone. So you can beach hop to all three Kennebunkport beaches… but frankly, Gooch’s is the best by a decent margin!
Have lunch at the Clam Shack.
Once you’ve soaked up a lot of salt air and need a break from roasting yourself in the sun, head back into downtown Kennebunkport for a delicious seafood meal at The Clam Shack.
Skip their lobster rolls: they’re trifling (who the hell puts a lobster roll on a hamburger bun?! Team hot dog bun for life).
But their fried clams are what they’re known for, and that’s absolutely what you should order.
Their fries and coleslaw aren’t half-bad, either!
Walk around the wharf and harbor.
Once you’ve had a filling meal, digest a little with a walk around the cute downtown area of Kennebunkport.
Since you’re already at the Clam Shack, start with a little wander around the wharf and marina area, where the Kennebunk River heads out to sea.
There are lots of beautiful buildings along this harbor area and the sailboats in the marina are beautiful when they bob in the waves.
Shop around the cute downtown of Kennebunkport.
There are also a lot of shops and galleries you could explore. A few places we enjoyed were:
- Dock Square Coffee House for an iced coffee pick-me-up after lots of time in the sun
- The Candyman for homemade fudge, salt water taffy, truffles, and all sorts of other sweet goodness!
- Fine Print Booksellers for a small but thoughtful selection of books that are perfect for beach reading
Drive to Point Walker.
Kennebunkport is famous for its Bush Compound summer home – you’ll see all sorts of Bush family regalia all over the town. They take it pretty seriously – even the Clam Shack is shilling Barbara Bush’s book!
If you’re curious to cast an eye on where the Bushes spend their summers, drive to Point Walker, about 10 minutes from downtown Kennebunkport. It’s absolutely stunning and you’ll be able to spot the Bush compound from here.
Have dinner at one of Kennebunkport’s finest.
Once you’ve had your fill of sightseeing, sand, and sun, it’s time to start thinking dinner. Luckily, Kennebunkport is a really thriving and bustling seaside town, and there are a lot of options.
So far, I’ve had you overdosing on seafood, so I’ll be sure to include a non-seafood option for dinner.
(And don’t worry – the next two days bring us to Portland, for a respite on seafood, before diving back into the seafood mania as we head up the coast!).
- Alisson’s Restaurant: while I may be biased to the name, this gets the best consistent reviews in town and it’s located conveniently right in Dock Square. They’re famous for their lobster poutine, which is just as decadent as it sounds! They also have lobster pizza and lobster mac ‘n cheese. It’s as Maine as it gets!
- Chez Rosa for casual, French-inspired seafood like moules frites as well as non-seafood options like beef bourgignon and French onion soup.
- Old Vines Wine Bar for expertly curated wines and small plates so you can sample your way through a delicious dinner.
Day 3: Portland
Have breakfast at Becky’s Diner.
One of Portland’s main institutions is Becky’s Diner, and you can’t go wrong following the crowds to eat one of th best, heartiest breakfasts in Portland!
Lines can be long, so arrive early and expect to wait. Don’t miss their wild blueberry pancakes!
Wander around the Old Port.
Becky’s Diner is a short walk from the Old Port neighborhood, so it’s time for a short walking tour of this charming part of town!
There are a lot of cool sights in this area; let me list a few favorites.
First, walk to the fisherman’s wharf area with lots of lobster traps and quintessential New England fisherman vibes.
If you walk from J’s Oysters via the back alleyway to Harbor Fish Market (also a great stop!), you’ll see this view that seems right out of a painting!
Another favorite area in the Old Port is the one stretch of street that remains cobblestoned with beautiful buildings surrounding it (pictured above at the start of this section).
You can find the cobblestoned street pictured above at the intersection of Fore Street and Silver Street but there are some other cobblestone streets around on the side streets in the area.
Getting hungry for a mid-morning snack? Grab Maine-style potato donuts (odd — and frankly not a favorite — but unique to Maine) at The Holy Donut.
Take a harbor cruise.
There are a few short cruises you can take that depart from the Old Port that explore beautiful Casco Bay.
While there are many islands you can access from Portland, on this coastal Maine itinerary we unfortunately don’t have time for that – even with 10 days in Maine!
Instead, hop on a boat for a quick harbor cruise!
I suggest the Diamond Pass run by Casco Bay Lines which leaves at 11 AM and takes 2 hours, returning at 1 PM.
Grab a quick bite before your brewery tour.
Next up on this itinerary is a brewery tour at 3 PM – but you don’t want to sample Portland’s best brews on an empty stomach!
Let’s grab a bite to eat in the Old Port area first so that you can remain conscious for the rest of this Maine itinerary!
There are a number of great restaurants in the Old Port area. Here are our top recommendations for you to choose from:
- Duckfat for delicious French fries fried in — you guessed it! — duck fat. Double up on the indulgence by having it as poutine, Canadian-style with cheese curds and gravy.
- Eventide Oyster Co. for tasty fresh oysters from all up and down New England as well as delicious lobster rolls
- The Thirsty Pig for tasty homemade sausages paired with excellent local beers
Go on a brewery tour.
Maine is burgeoning as a craft beer destination, and Portland is at the very heart of it! There are a number of breweries in Portland proper, as well as many breweries elsewhere in Maine that have pubs and offerings in Portland.
You could do a self-guided tour of a few of Portland’s breweries, but frankly, it’s a lot more fun to do a brewery crawl!
This brewery tour starts at 3 PM and will take you to several of the best breweries in Portland on a guided walking tour. You’ll get to sample several beers at each stop and see a great representative sampling of the Portland, Maine brewing scene.
Walk up and over Munjoy Hill.
After all those beers, it’s time to sober up with a walk through one of Portland’s most scenic and beautiful communities: Munjoy Hill.
Yes, it is a hill, and it is a bit steep, but it’s really worth the walk as this is one of the coolest neighborhoods in Portland.
Once you reach the crest of Munjoy Hill, there is a cool observatory tower called the Portland Observatory. It’s a historic maritime signal tower that was built in 1807, and it’s the only remaining tower of this type made of wood known in the United States!
Bonus: there’s also a museum inside, and you can ascend the observatory tower for fantastic views over all of Portland! It costs $10 and includes a tour.
Note: If you do the brewery tour, you will arrive here too late to do the tour as the tower closes at 4:30 PM, but you can see the exterior and maybe head back here on another day if you want to ascend the top and do the museum tour
Head down to the water’s edge.
Once you arrive down at the water, you’ll find the Cleeve-Tucker Memorial marking the end of Portland’s East End neighborhood.
Along the water’s edge, you’ll find a lot of cool food trucks here!
There’s also East End Beach (rather a small beach, but it is possible to go for a dip here) and Fort Allen Park, which offer incredible views over Casco Bay.
Have a delicious dinner in Portland.
As you can see, Portland is all about eating your way through the city!
I’ve already recommended a lot of places above, so you can choose from one of the other sections.
If you want other suggestions, I’d pick: Sichuan Kitchen for delightfully authentic “ma la” spicy Chinese food from the Sichuan province, Boda for Thai street-style eats, or Central Provisions for trendy cocktails and small plates.
Day 4: Portland
Spend the morning on Washington Ave.
Like its West Coast sister city of the same name, Portland, ME is becoming a hipster-topia.
Nowhere else is that more obvious than on Washington Avenue in South Portland!
Start the day with a delicious breakfast at Portland Pottery Café, a hybrid pottery shop and café.
Their biscuits and gravy is obscenely large and obscenely delicious!
They also have a selection of great sandwiches if you’re not feeling particularly breakfast-y. The Figgy Piggy is also delicious: fig jam, prosciutto, what could go wrong?
Alternately, you could get a bagel at Forage, which looked really vibrant and popular with locals.
After breakfast, wander down Washington Avenue and explore some of the cool small businesses that have popped up here. Here are a few favorites.
- Maine & Loire: a wine shop with a great selection of wines, though at a high price (I wish there were more mid-budget options)
- The Cheese Shop of Portland: exactly what it sounds like — a delicious local cheese shop with a great selection
- Maine Mead Works for mead (a fermented drink made of honey water!) and Oxbow for beers, particularly their sours
Drive to Portland Head Light House.
Located in Fort Williams Park, the Portland Head Lighthouse is an absolute can’t-miss on any Maine itinerary. Of all the lighthouses in Maine I saw, this one was my favorite!
The lighthouse is exquisite and there is a coastal trail where you can see a few different viewpoints of the lighthouse with different compositions, which is great for photographers.
There is also a cliff trail that goes on the other side of it, and there is an area where you can walk down to the beach if you want to swim in the water with lighthouse views behind you!
There are also a handful of food trucks in the area: I saw one gelato shop and two lobster shack style restaurants selling seafood sandwiches and fried seafood.
However, I have you getting lunch at the next destination, so only grab something to eat if you’re super hungry or planning to skip the next destination on this list.
Parking is $2 per hour with a minimum of 2 hours (so effectively $4 – honestly, you won’t really want to spend more than two hours here, and even that is pushing it).
Have lunch at Two Lights in Cape Elizabeth.
Two Lights is the name of both a lighthouse and a state park in the Cape Elizabeth area south of Portland.
Two Lights is so named because there are two lighthouses that look almost like twins about 300 meters from each other. You can see them at the same time, but they are not as close together as I expected.
If you want something to eat, I recommend heading towards The Lobster Shack at Two Lights.
Near the seafood shack, there is a small coastal path where you can walk out to get a better view of the lighthouses as well as a small cove where you could swim if you’ve brought your bathing suit.
Visit the Arts District and Portland Art Museum.
After exploring the Southern Portland area, it’s time to head back to downtown Portland: particularly the Arts District which is centered around the Portland Museum of Art.
This is one of my favorite areas in all of Portland. It’s artsy and funky, it’s full of great local small businesses, and there’s a lot of old-fashioned architecture given new life by the upstart businesses occupying there.
Here are a few of my favorite places in the Arts District area:
- Speckled Ax for wood-roasted coffee — it’s quite unique, I haven’t had anything like it!
- Yes Books for a wonderful selection of secondhand books
- Flea For All for a great flea market on Fridays and Saturdays
After strolling around the Arts District area, you may or may not want to go to the Portland Museum of Art, depending on time, budget, and your interest in art.
The next activity on this list is also a museum, so you may want to opt for one over the other.
Portland Art Museum costs $18 and contains art ranging from 18th century works through to contemporary art.
Do a tour of Victoria Mansion.
The next place is a short walk away from the Portland Museum of Art but it feels a world away!
While the Portland Museum of Art is rather contemporary, the Victoria Mansion is elegant and old-fashioned, almost untouched over the last 200 years.
You can take a tour of the mansion – the final tour finishes at 3:50 PM (summer hours), or you can just check it out from outside if you are on a budget or are not interested in seeing the interior museum.
Tours are required and tickets cost $16. Booking in advance is recommended, particularly on weekends and rainy days.
Explore the neighborhood.
The area around Victoria Mansion is perhaps even more beautiful than the mansion itself! This is where I found virtually all of my favorite buildings in Portland.
Don’t miss the rainbow-colored row of townhouses (formerly carriage houses, I believe) which are just kitty-corner from Victoria Mansion. It looks almost like Rue Cremieux in Paris, minus the crowds!
Eat in downtown or head back to Washington Ave for drinks and dinner.
After a full day exploring downtown Portland, you have two areas where you could get a delicious dinner.
If you don’t want to leave the downtown area you’re currently in, here are the places I suggest: Bao Bao Dumpling House (a few blocks away from Victoria Mansion) or Sichuan Kitchen.
Alternately, you can head back to Washington Avenue for some more exploration of this charming part of town! There are a lot of great restaurants that are open for dinner here, many of which are Portland favorites.
- Duckfat for poutine if you didn’t already have it at the other branch in Old Port.
- Cong Tu Bot for delicious Vietnamese food like bun cha (pork patties served with herbs and dipping sauce)
- Terlingua for Mexican food
Day 5: Mid-Coast Maine (Freeport, Brunswick, Harpswell & Islands)
Stop at the outlets in Freeport.
If you want to do a little morning shopping, head to the town of Freeport which is known for its outlets and massive L.L. Bean.
Take a photo with the giant Bean Boot — it’s cheesy, yes, but it’s a Maine must!
There are a number of good outlets, and I snagged a 40% off blazer at J. Crew, some of my favorite Smartwool socks from L.L. Bean… and tore myself away from the Loft outlet, because my credit card was weeping.
Take a stroll in Brunswick.
Brunswick is a delightful small city in Maine with a vibrant Maine Street (hopefully you enjoy the pun as much as I do) and great shopping and activities.
It’s home to Bowdoin College and as a result, there are a lot of businesses that cater to its large student population, and the town has a younger feel than other places in Maine.
There is a surprising amount to do in Brunswick!
Take a walk by the Sea Dog Brewing Company on the Frank J Wood bridge (stop and admire the falls on the other side) to the Topsham side of town, and then take the pedestrian swinging bridge over the river back to Brunswick.
On your way back, walk past Fort Andross (and pop into the flea market there), or go shopping on Maine Street.
Grab something to eat in Brunswick before you go: I suggest Sweet Angel for Thai! It’s not on Maine Street, but it’s worth the detour. Currently, they are doing take-out only.
Take a hike on Orr’s Island.
After you’ve grabbed something to eat in Brunswick, it’s time to burn off that lunch with a hike!
Devil’s Back in Orr’s Island sounds intense, but it’s a relatively easy hike that is incredibly beautiful. It’s just 2.5-miles round trip with 200 feet of elevation gain, so rest easy that it’s not too strenuous!
Kayak around Bailey Island and stop at Cook’s for lunch.
If you haven’t exhausted yourself with all that hiking and eating, it’s time for one of my favorite things to do in Maine in summer: sea kayaking!
Luckily, you can rent kayaks easily at the rental company stand outside of Salt Cod Café, technically on Orr’s Island but located right next to the cool bridge to Bailey Island.
You could grab a bite to eat at Salt Cod Café, but I recommend saving your appetite for a delicious lobster feast at Cook’s after you kayaking!
Check out the Giant Steps and Land’s End for a great view.
Once you’ve returned your kayak and had a delicious lunch, it’s time to explore a bit more of Bailey Island. Luckily the island is very small, so it’s pretty easy to see the best of Bailey Island in a quick visit.
First, head to the Giant Steps. This is a short trail where you can see some cool rock formations: a set of volcanic rocks that look like a staircase that perhaps could have been used by a giant!
After, drive to the end of Bailey Island at Land’s End. Here, there is a small gift store, a memorial to drowned and lost fisherman, and stunning views of other islands further out in Casco Bay.
Finally, on your way back, be sure to stop at Mackerel Cove. This is one of the main harbors in Bailey Island and has an incredible view!
Grab ice cream at Pammy’s.
I know this coastal Maine itinerary is full of food… but that’s the kind of traveler I am (and I hope you are too!)
It may seem crazy to say ‘dessert first’ but I think the vibe of Pammy’s is even more fun during the day.
When we went there was some live music and it was really pleasant to sit in the pink-painted Adirondack chairs and admire Pammy’s vision for her ice cream shop.
I got the coffee heath bar sundae and it was DELICIOUS.
Have dinner at Dolphin Marina & Restaurant.
Finally, it’s time for dinner at one of my favorite restaurants in Maine: Dolphin Marina & Restaurant.
This is a spectacular place for sunset views because it’s out on one of Maine’s “fingers” and therefore is one of those rare East Coast spots that has a spectacular sunset view.
The food is also excellent. I had a jerk salmon sandwich with chili slaw and jammy roasted tomatoes – it was divine. We also split the crab cakes, which I could have eaten a half dozen of…. easily.
I suggest getting to Dolphin Marina & Restaurant about 1.5-2 hours before sunset. It’s really busy and it takes a while to get your table.
Luckily, there is a great bar area and you can grab a drink while you wait and there are plenty of places to walk and sit with a drink while you wait.
Aim to finish up your meal just before sunset so you can take a walk on the grounds and admire views like those above!
Day 6: Mid-Coast Maine (Bath, Wiscasset, Damariscotta, Georgetown)
Head to the charming town of Bath.
Of all the towns in Maine to choose from, Bath is up there as one of the most charming.
Take a walk down Main Street, stop in some bookstores or shops, and peruse to your heart’s content.
If you’re thinking breakfast, I suggest just getting a small pastry from Cafe Creme or Mae’s Cafe & Bakery, because Maine’s largest lobster roll is waiting for you at our next stop!
Wander through Wiscasset.
Route 1 runs through it, and you could blink and miss it — but the charming town of Wiscasset is definitely worth the stop!
Wiscasset is one of those towns that is like a living museum. There are a lot of information placards throughout the city that showcase all the different architectural styles and buildings and their historical importance.
Another cool place to visit in Wiscasset is the Butter Mold Company. It’s a very unique place where they still make butter molds from scratch.
Bonus: everything there smells like cinnamon and apple pie. The owner is also extremely nice and great to chat with.
Grab one of Maine’s most famous lobster rolls.
Wiscasset is best-known for its famous lobster shack, Red’s Eats. Frankly, there is always a huge line, and the price is not cheap.
The market price for a lobster roll was $35 when I went, compared to other places where it was $20-30!) – but their lobster rolls are massive, about double the size of other ones.
I made a mistake and didn’t wait in line at Red’s (I’m a bit contrarian about lines) and went to Sprague’s instead and got a crab roll. It was disappointing. Do as I say, not as I do, unless you also like disappointment.
Shop in Damariscotta.
There are a bunch of great boutiques and art galleries in Damariscotta.
In fact, of all the places I shopped at in Maine (which was a devastatingly highly number), my favorite stores were in tiny little Damariscotta, and I even wrote a whole post on this charming small town!
There’s a great brand-new store called Wildings that I highly recommend. It’s hard not to leave with half the store! If you’re a millennial who loves plants, pots, jewelry, and quirky accessories, you’ll be hard-pressed not to leave without a maxed-out card.
Other things to do in Damariscotta include checking out the excellent bookstore and grabbing a cup of coffee at the adjoining café, walking around the pretty wharf, or visiting the oyster midden.
Wait, oyster midden? An oyster midden is a small ‘mountain’ of oyster shells left behind by the Native Americans who lived in this region for centuries. You can find one unperturbed midden at this park!
Have dinner at Five Islands.
From Wiscasset to Five Islands Lobster Co. in the peaceful town of Georgetown, Maine is quite a trek… but it is worth it. It’s one of the most beautiful restaurants in Maine, hands down!
They serve delicious fried fish sandwiches and lobster rolls (get yours with cilantro mayo!), perfect onion rings, and exquisite steamed lobster dinners.
The setting, though, almost edges out the food as the main draw. It’s one of the most beautiful harbors in all of Maine, with boats bobbing amidst a close cluster of, well, five islands.
One caveat: mosquitos LOVE this place, more than anywhere else I went in Maine. And according to the people I went with, it’s always that way. Bring lots of mosquito repellent and suck it up!
Day 7: Rockland
Visit the Olson House in Cushing.
If you’re a fan of Andrew Wyeth, I strongly recommend making a detour to Cushing to visit the Olson House.
When we visited, a majestic black and white horse was just grazing in front of the house, and he came right up to us for pets and scratches!
This is where he painted his most seminal work, Christina’s World, as well as innumerable other paintings over his nearly 20 years living on the grounds.
The grounds and the house are currently closed for renovations, but you can still see the house from the field from afar, and you can visit his gravestone.
Cushing is a brief 15-minute detour off of Highway 1 on the way ro Rockland, so it’s not a huge sacrifice for a big art history lover.
However, if you don’t have much interest in Wyeth or pastoral landscapes, you can safely skip this part of the itinerary.
Have breakfast at a Rockland Cafe.
Upon arriving in Rockland, it’s time to grab a bite to eat at one of the many cafés in this charming town.
There are a number of places serving breakfast pastries; I suggest Atlantic Baking Co.
Visit the Farnsworth Art Museum.
Rockland is considered the Art Capital of Maine and with good reason: the Farnsworth Museum is one of the best art museums in the country!
The Farnsworth Museum has a rich collection of Andrew Wyeth works as well as gifts from the Wyeth family, recently bequeathed by Andrew Wyeth’s late widow and muse Betsy Wyeth, who passed away in 2020.
There is also a large collection of contemporary art by Mainers and other New England artists.
Stroll and shop down Main Street.
Rockland is an arty little town and that extends beyond just the Farnsworth!
There are a number of excellent galleries and boutiques that are worth window shopping — or entering, if your wallet dares!
Grab a beer at Rock Harbor Pub & Brewery.
Once you’ve had your fill of Rockland, grab a drink and maybe a bite to eat at the Rock Harbor Pub & Brewery.
Don’t have too late a night — we’re going to wake up bright and early for a morning hike tomorrow!
Day 8: Camden
Take a hike in Camden Hills State Park.
Camden is best known for its beautiful state park, Camden Hills State Park, just a few miles north of the city of Camden but feeling like a world away!
Camden Hills State Park has a lot of wonderful hiking trails available. You could hike up the trail to Mt. Battie (it’s about 3.1 miles with 800 feet of elevation gain).
You can also drive up to the summit if you’re unable to hike… no shame or judgment here: these beautiful views are for everyone!
At the top of Mount Battie, you’ll be treated to incredible views over Camden Harbor and the islands off the coast of the mainland dotting Penobscot Bay. It’s spectacular and you’ll absolutely want to spend some time up here, relaxing, meditating, taking pictures, perhaps eating a picnic lunch if you hiked.
From Mount Battie, you can even spot Cadillac Mountain on Mount Desert Island off in the distance on a clear day!
For a much more intense hike, Mount Megunticook is an option. It’s a moderate hike, 3.8 miles roundtrip with about 1,000 feet of elevation gain (and then of course, just as much elevation in descent). Bring lots of water and a snack, and be prepared for Read trail reports here.
Unfortunately, during my visit to Maine I was having a chronic pain flare-up and wasn’t able to hike, but my friend has hiked Megunticook several times and insists it’s one of the most beautiful hikes in Maine.
Grab a bite to eat.
After your Camden Hills exploration, you’ll probably be hungry.
We wanted to eat at Merriner’s, which is excellent and came highly recommended by my friend, but we arrived too late (lunch ends at 2 PM!).
Instead, we had a Cuban sandwich next door at Camden Café and it was delicious – and the views of the harbor are impossible to beat.
Stroll and shop in downtown Camden.
Camden is one of the most charming small towns in coastal Maine and there is so much to do and see in Camden that I’ve written in a blog post here!
You should definitely spend some time walking around the Harbor area and the Harbor Park, shopping at some of the shops on Main Street and Bay View Avenue, and admiring Megunticook Falls in the harbor.
Take an afternoon swim at Laite Memorial Beach.
If you’re feeling hot and sticky after all that hiking and walking and eating, it’s time to refresh yourself in the small but lovely beach just beside the harbor at Laite Memorial Beach.
It’s not the largest beach nor the most beautiful, but I loved going for a cool refreshing dip on the sandy/pebbly beach and bobbing in the water with sailboats off in the distance. It was magical.
Go sailing on the bay.
Finish your magical day in Camden in the most magical way: on the sea on a boat cruise to explore the Bay and even get to see the beautiful Curtis Lighthouse on an island off the shore.
You may also get to see wildlife like seals, cormorants, porpoises, and more – and perhaps even some lobstermen pulling in their traps!
Day 9: Bar Harbor & Acadia National Park
Drive to Mount Desert Island and visit Sand Beach.
Let’s leave Camden bright and early to make our way to our final stop on this coastal Maine itinerary: Mount Desert Island, home to Acadia National Park.
Once you arrive at Mount Desert Island and check into your Bar Harbor hotel, it’s time to hit the ground running… or relaxing!
Since this itinerary has been pretty fast-paced, I think a little relaxation by the ocean is in order.
Although most of Mount Desert Island’s coastline is composed of rocky cliff faces (like much of Maine), there is one sandy ocean beach hidden inside Acadia National Park for all to enjoy!
Sand Beach is about a 20-minute drive from the Bar Harbor town center and is one of the first attractions along the Park Loop Road. The parking area tends to fill up quickly, so be prepared to scout for a parking spot.
The beach is staffed with park lifeguards to make swimming in the chilly water safe for all the brave souls that choose to do so. Though lately, Maine’s water has been warmer than ever before… a bittersweet side effect of the sad reality of global warming.
Sand Beach is the perfect spot to set up for a sunny afternoon with a picnic, beach chairs, and plenty of sunblock — that New England summer sun is no joke!
Hit one of the hiking trails.
If you’re not interested in swimming, there’s still plenty to do in this area, such as searching through tide pools and walking the shoreline to search for shells.
There are a couple of fun trails that take off from this area too. One of the nearby trailheads is for the Great Head Loop Trail, which starts on the east side of Sand Beach.
The shorter loop option is 1.6 miles around and offers spectacular panoramic views of the area, including a scenic overlook of Sand Beach.
If you want to add a more challenging hike to your Acadia itinerary on the first day, the trailhead for the Beehive Trail, a tough but rewarding 1.6-mile loop, is located right near Sand Beach.
It uses iron rungs to climb up the more difficult part of the trail. Be extremely careful here as some hikers have died. Do not descend the same way you ascended.
If you begin the hike, be prepared to finish it so that you do not endanger people who are coming up the iron rungs. This is not one for those with a fear of heights!
Stroll around Bar Harbor.
After soaking up the sun and relaxing the afternoon away, it’s time to head into town and enjoy all the cool things to do in Bar Harbor!
Bar Harbor is a charming New England coastal community with quirky boutique shops and amazing seafood restaurants.
Before dinner, take a walk along the Shore Path, which begins at the Town Pier. This short path offers beautiful views of the boats anchored in the harbor for the evening.
Have dinner at The Terrace Grille
Dine right on the water at this gorgeous restaurant!
The outdoor seating is decorated with beautiful yellow umbrellas and offers five-star views of Frenchman Bay and the Porcupine Islands. Not only are the views great, but the food is too!
Keep it classic with a boiled Maine lobster or indulge and order the Maine Lobster Bake.
The portion size is no joke, and definitely not for one: it comes with all the goods including New England clam chowder, steamed mussels and clams, over one pound of Maine Lobster, seasonal sides, and homemade blueberry pie!
Grab a cone at Mount Desert Island Ice Cream
Hope you saved room for dessert. Is any evening by the ocean complete without an ice cream cone? You already know the answer to that question!
The ice cream from Mount Desert Island Ice Cream is unlike any you’ve had before. Maybe it’s the premium flavors mixed with the ocean air, or maybe it’s the care that goes into every homemade batch. Yum!
Day 10: Acadia National Park
Drive the Park Loop Road
Roll the windows down and let in that warm sea breeze as you head out to tour Acadia’s Park Loop Road.
The 27-mile road loops around Acadia National Park, and it is one of the best scenic drives in Maine, taking you from the ocean to the mountains and everywhere in between.
Set aside at least half a day to make the drive. There are lots of places to stop along the way, but here are some of the best sights.
Stop at Sieur des Monts.
Sieur de Monts is the heart of Acadia National Park and one of the first attractions you’ll see when driving the scenic Park Loop Road.
This area is home to many sights, including the Sieur de Monts Spring, Acadia Nature Center, Wild Gardens of Acadia, Abbe Museum, and historic memorial paths.
See Thunder Hole with your own eyes (and ears!)
Thunder Hole is named after the booming sound like thunder that the ocean waves make as they slam against the rocky shore.
The force of the wave pushes air and settled water to the surface, creating a loud “thunderclap” made of water.
The small rocky inlet at Thunder Hole may not be as wild at low tide, so don’t be disappointed if you see it and it doesn’t live up to its name.
Check a tide chart and wait for some choppy water to come in with the high tide, and you’re sure to hear what all the hype is about.
Marvel at the views at Otter Point.
Less than a mile past Thunder Hole, there will be a parking area for Otter Point.
This rocky shoreline is named after Acadia National Park’s spunky river otters. The most impressive feature at this stop is Otter Cliff, which stands an impressive 110 ft high!
This is a great spot to hang out in the sun and watch the ocean waves crash over the rocks.
Lunch at Jordan Pond House Restaurant
After a morning of sightseeing, it’s time for a well-earned lunch break.
Famous for their mouth-watering popovers, the Jordan Pond House Restaurant is every foodie’s dream come true.
Take a hike around Jordan Pond Loop Trail.
After all that eating I’ve had you doing on this trip, It’s time to get a little hike in. Wouldn’t you agree?
The beautiful 3.5-mile loop trail around Jordan Pond is the perfect place. This scenic hike will take you along the shore of the pond, on a flat but rocky trail. Sturdy shoes are recommended for this trail.
Head home to end your time in Vacationland.
Whether you make the long drive back home or to Boston, or the shorter drive to Bangor to drop off your rental car and catch a flight, it’s time to say “see you soon” to Maine.
Make your plans to come back to Maine in other seasons. You’ve seen the glory of the summery coast. Plan to see the riotous fall colors or experience the desolate but sublime winter beauty.
Know that it’s not goodbye, but rather see you later: your first trip to Maine is just the beginning of a lifelong love!
