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When it comes to cute small towns, Maine is NOT in short supply! Maine’s unbridled natural beauty provides the perfect backdrop for pretty spots across the state, but some towns really go above and beyond to crank up that charm factor!
From the beautiful islands and gorgeous beaches of the coast to the unspoiled landscapes and striking waterfalls of the interior, there are lovely little communities situated all around Maine. It was hard to narrow it down, but we think we’ve picked out the best of the best, the most charming of all the charming, the very sweetest spots in the entire state. If you’re looking to visit a town that is photogenically fabulous and full of small-town appeal, then you should consider a visit to one of the 10 cutest small towns in Maine!
One of the Penobscot Bay region’s finest gems is Rockland, a lovely little town known for its vibrant art scene, its quintessential downtown USA vibe, and for being the home of the beautiful Rockland Breakwater Lighthouse. There are plenty of great things to do in Rockland, but if you’re not checking out some of the local art in this darling little town, you’re missing out! There’s Farnsworth Art Museum, the Center for Maine Contemporary Art, The Muir Garden for Contemporary Sculpture at Harbor Square Gallery, and several other opportunities for seeing Maine-made art around Rockland.
Just as with all coastal communities in Maine, Rockland takes pride in its connection to the sea. Every summer, people travel from all around for the 4-day Maine Lobster Festival for live entertainment, games, and of course, some fresh-caught, extra yummy lobstah! You can also get out on the water with a Maine Windjammer Cruise, a great way to experience maritime culture for yourself.There are also plenty of options for where to stay while in Rockland, but just a few miles up the road is the Samoset Resort in Rockport, a gorgeous sea-side resort that makes for a perfect landing spot after a long day of exploring adorable Rockland.
Next up is the little coastal town of York, situated on the Southern Maine coast and known for its beautiful beaches; York is even considered one of the best places to catch the sunrise in coastal Maine! Dubbed “The Yorks,” there’s York Village, York Harbor, York Beach, and Cape Neddick, each with its own distinctive flavor of charm to draw you in. York Village is the historic downtown where you will find adorable shops, restaurants, cafes, and carefully preserved historical buildings to explore like the Old Gaol, Maine’s first prison that was originally built in 1656.
York Harbor offers spectacular water views as you enjoy the Cliff Walk or stay in style at the York Harbor Inn, where Maine simplicity meets luxury. Long Sands Beach and Short Sands Beach are must-visit York beaches, and Cape Neddick “Nubble” Lighthouse is a definite must-see as one of the most famous lighthouses on the east coast; while there is no public access, it makes for a stunning photograph in any season. York basically oozes small-town charm everywhere you turn… all in the very best ways!
Old Orchard Beach, ME
Affectionately dubbed “OOB,” Old Orchard Beach is an absolutely adorable beachside town that gives off all the classic New England beach community vibes! Seven miles of beautiful beach awaits you, whether you’re interested in splashing around in the bracing ocean water, soaking in the sun on the sandy shore, or checking out the entertainment on The Pier, the distinctive 500-foot wooden pier that houses restaurants, food vendors, souvenir shops, and a nightclub with a phenomenal view of the Atlantic!
OOB is also home to New England’s last surviving beachfront amusement park, Palace Playland, featuring several rides and attractions, including the 20,000 sq ft+ arcade that houses vintage and modern arcade games, photo booths, and so much more! When looking for where to stay, check out Alouette Beach Resort for options that range between comfort economy and deluxe luxury suites that offer stellar ocean views and top-of-the-line amenities. Old Orchard Beach is a delightful taste of classic New England beach community with a full serving of modern fun!
Moving inland, the Rangeley Lakes region is home to one town, in particular, that is the heart and soul of this area, a town full of non-fussy Maine charm that is waiting to surpass all your expectations: its namesake, Rangeley. This popular vacation destination is one of the best places to visit in Maine (and one of the best places in the state to spot a moose!) and is all about the outdoors, with activities that include canoeing, boating, swimming, and hiking in the warmer months, and snowshoeing, cross-country skiing, fat biking, and ice fishing in the winter; Maine’s well-known for its awesome winter activities, and Rangeley is the perfect place to experience them!
The Rangeley Lakes Scenic Byway is also one of the best routes to get a healthy dose of Maine’s fabulous fall foliage, so this cute little town is an attractive vacation spot any time of year. Stores like the Ecopelagicon offer locally produced Maine goodies like Maple syrup, blueberry jam, and a line of skincare products from Rangeley Balsam that makes good use of the balsam firs that provide the gorgeous green backdrop of Rangeley. There are plenty of great places to eat in this cute little town, but if you happen to stay at the rustically charming Loon Lodge Inn (and you really should look into it!), then you can easily sample their delicious menu that features locally-sourced meats and produce and is considered a Rangeley staple.
Bar Harbor, ME
Beautiful Bar Harbor has one of the loveliest downtowns in all of New England, and that is saying a lot! This gorgeous town is located on Mount Desert Island and is often referred to as the “gateway to Acadia National Park,” and an absolutely delightful gateway, it is! There is so much to do in Bar Harbor, with stunning ocean views and incredible natural attractions like Thunder Hole, the rocky inlet where water rushes in with a loud BOOM and splashes and sprays up a good 40-feet high, stunning beaches that are begging to be enjoyed, and awesome hikes that span Acadia National Park.
Downtown Bar Harbor is super cute with a great selection of shops and restaurants to choose from, and the local winery, Bar Harbor Cellars, even made it on this list of must-visit New England wineries!
As for where to stay in Bar Harbor, you have some excellent options, including some pretty neat Airbnbs in Bar Harbor and Acadia. A visit to Bar Harbor is absolutely lovely however you plan it, but feel free to follow this ready-made 3-day itinerary for Bar Harbor and Acadia National Park if you’d like something that’s already all set up for you!
With a town motto like “Beautiful Place by the Sea,” Ogunquit is an easy pick for one of the cutest small towns in Maine! Ogunquit has 3.5 miles of soft sand beaches with stunning ocean views and an absolutely incredible- and very easily walkable- downtown area that offers adorable shops, lovely art galleries, and lots of fantastic eateries to check out! If it’s live entertainment you’re in the mood for, check out the Ogunquit Playhouse, one of the essential must-dos in this Maine travel guide!
Being a resort town, Ogunquit has plenty of phenomenal options for where to stay, but if you’re looking for something that radiates seaside village charm, is an easy walk to both downtown and the beach, and has plenty of practical and luxurious amenities, The Admiral’s Inn might just be the perfect spot for you! Pools (and a poolside patio bar!), hot tubs, dry sauna, full gym, seasonal fire pit, and an on-site massage therapist await you to take your visit in gorgeous Ogunquit from very good to very great!
Boothbay Harbor, ME
Another gem on Maine’s stunning coast, Boothbay Harbor draws people in from far and wide that want to experience the charms of this protected harbor town. There are so many awesome things to do in Boothbay Harbor, but one of its keystone events is the Boothbay Harbor Windjammer Days festival that celebrates and honors the region’s rich maritime history with fun festivities like live musical entertainment, an antique boat parade, fireworks over the harbor, and delicious local food favorites. You can even take a Puffins Cruise out of Boothbay Harbor with Cap’n Fish’s Cruises to see where wild puffins nest (Maine is the only state in the US where you can see this!) or take a combo whale watching/puffins tour. Getting out on the water is always a great time, right?
Downtown you’ll find shopping, museums, wonderful inns and hotels, and plenty of fabulous restaurants to choose from, but if you leave Boothbay Harbor without sampling some of their fresh-caught lobster, you’re making a mistake! In fact, at Boothbay Lobster Wharf, you can watch as the fishermen pull in and unload their daily lobster take, choose which lobster you want for yourself, and the people at Boothbay Lobster Wharf will cook it up for you! Doesn’t get any fresher than that, does it?
Back inland and tucked away on the edge of the White Mountain National Forest, is a darling little town that is situated on one of the most scenic driving routes in Maine: Bethel. This quaint mountain village is the perfect blend of peaceful tranquility and active lifestyle, with people traveling to Bethel all times of the year to enjoy the magnificent scenery and participate in the outdoor activities that are available during different seasons like hiking, kayaking, and fishing in the warmer months and winter fun, playing in the snow at Sunday River Ski Resort! Nearby Grafton Notch State Park is also a great outdoors destination with waterfalls to ooh and ahh over and excellent hiking trails to explore.
There are fantastically unique shops and galleries in this cute mountain resort town, like Elements Art Gallery, where you can go to peruse local art and craftsmanship (everything in the store is made in Maine!) and pick up a souvenir or three to take a little piece of Bethel home with you. When it comes to restaurants in town, you have your pick, but Sunday River Brewing Company needs to be in the mix somewhere; with artisan-fired pizzas and donuts that are made fresh daily, you’ll go for the food and then remember that oh yeah, you’re in a brewery and the craft beer on tap is also incredible! As far as where to stay in Bethel, that just depends on if you’re looking for a B&B vibe, a mountain inn, a nice hotel, or a waterfront Airbnb, but options are aplenty there, too for where to lay your head in this adorable mountain village.
A part of the slower-paced area of the coast referred to as the Damariscotta Region, the darling little town of Damariscotta is an idyllic respite from some of the more crowded coastal favorites. This lovely village has not one, but TWO annual oyster festivals that pay homage to the oyster industry that has kept Damariscotta prosperous over many generations, and the Whaleback Shell Midden State Historic Site offers an interesting up-close look at a massive midden, or oyster shell heap, left behind from the Native people of this area hundreds of years ago. You can also tour the glistening Damariscotta River on a Sunset Cruise, cocktail in hand as the sun sets slowly in the Maine sky, or perhaps an Oyster and Wine Tasting Cruise so you can taste the fresh oysters that this region is so proud of!
Damariscotta has a quaint yet vibrant downtown area that offers a peek into simplistic Maine style without the kitschy vibe of some of the busier resort towns, with great shops like Maine Coast Book Shop and Café and Sheepscot River Pottery for you to explore. There are many excellent options for where to stay and eat while in the Damariscotta region, but just about 10 minutes up the road is the little town of Wiscasset, where you can find a lobster roll at popular Red’s Eats that will be well worth the line you will likely have to stand in to order from this quintessential Maine lobster shack!
Kennebunkport absolutely had to be on our list of cutest small towns in Maine because, well, it’s probably one of the cutest small towns in the entire United States, period! Quaint, adorable, lovely, independent, charming, basically all of the things that come to mind when thinking about small-town charm! This sweet little seaside town has so much to offer: beautiful beaches, boutique shopping downtown, a fabulous selection of year-round restaurants and charming inns, B&Bs, and hotels, and plenty to do and see in Kennebunkport.
While Kennebunkport is perhaps most well-known for being home to the Bush family’s summer estate, this coastal town is welcoming and friendly to all, with a variety of natural attractions, tours (some of the best whale-watching in Maine), and man-made sights to look into- check out the Wedding Cake House, it’s adorable!- one thing that isn’t likely to happen in Kennebunkport is boredom.
If you’re looking for a unique twist for your stay, look into glamping at Sandy Pines Campground… interesting tent and cabin options and great amenities (saltwater pool and smores kits? Heck yes!) equals laidback fun in comfort and style; plus, glamping is a little kinder on the wallet than some of the pricier resort-style accommodations in the area can be!
Whether it’s one of the coastal resort communities or the inland gems, Maine is full of adorable little towns, but we’ve done our best here to pull together the top 10 cutest small towns in Maine so you can choose for yourself which spot is calling your name for your next Maine getaway. Wherever you end up, happy travels!
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Amy is the founder of New England with love. A proud Vermonter, she hopes to share her love of New England and help you find the best adventures in the region. Amy is also blogger/founder at Two Drifters, where she writes alongside her husband about romantic and couples travel, relationships, honeymoons, and more. When not working on websites, Amy is probably reading, cuddling with her husband and cats, & drinking a maple latte.