Maine’s underrated towns exude as much nonchalance as novelty, from the highlands to the islands. Those that made our list aren’t underrated as much as they are under the radar.
What if we told you that these towns offer everything you dream about in a Maine vacation without the crowds, kitsch, or cars bumper-to-bumper?
The beauty of visiting Maine can be found in cities that take a little bit of work to find. While Maine carries the Vacationland moniker, there’s a new vacation tucked away in mid-coast peninsulas and lakes that don’t start with Sebago.
Let’s head off the beaten path and explore Maine’s underrated and timelessly dated towns.
Allagash
Allagash is at the mouth of the famed Allagash Wilderness Waterway, a famed 92-mile water route that inspired Henry David Thoreau to write a book about his adventures.
Allagash also overlaps with the St. John River, making water adventures span in three directions and the Canadian border on the fourth side.
On a good day, you’ll see more moose than people. Strip malls are replaced with various outdoor tour companies ready to make your wilderness dreams come true.
Take a ride on the St. John Valley/Fish River Scenic Byway for fall foliage you just can’t get in Kennebunk. If you like Allagash, you’ll love the rest of Aroostook County.
Related: Exploring Maine’s 10 Most Scenic Towns Across the State
Castine
Those heading to Acadia National Park often overlook the Castine (“cass-teen”) exit on Route 1. If you take the turn on Castine Road, you’ll find a record that pre-dated the Plymouth colonies and takes you through major wars, a robust French trading port, and a summer destination for New England’s elite through the Great Depression.
This waterfront town on the Penobscot River houses the Maine Maritime Academy and an enclave of restaurants, shops, and historic inns.
Castine even has its own sandy beach that once served as a British landing point during the Revolutionary War.
Fortune and Travel & Leisure magazines also give this underrated town accolades for its inherent charm and scenery.
Harpswell
Harpswell stands out as almost a mini-Maine within the state as it covers peninsulas, road-connected islands, and hundreds of offshore islands.
Everything you want in a Maine vacation is here – sandy beaches, rocky cliffs, peaceful trails, overflowing lobster rolls, kayaking, boating, fishing, and so much more.
The Harpswell Heritage Land Trust properties give easy access with no packed parking lots and the only Giant’s Stairs in Maine.
If that isn’t dreamy enough, how about a McDreamy reason? This is the town where Maine native Patrick Dempsey married his wife and came back 19 years later to celebrate.
Planning a wedding? Their venue is available!
Houlton
Houlton holds the spot as the most up-and-coming town in Maine for the 2024 Solar Eclipse. Those preparations will pay off for years to come as the world is introduced to everything this Aroostook County town offers.
This town is easy to access as the “end of the road” for I-95, but there are still plenty of trails (water, dirt, and snow) to explore for a taste of Maine’s outdoors.
The walkable Market Square mixes river crossings, restaurants, and relaxation for a quintessential Maine experience.
Whether you want to go four miles to Canada or 55 miles to the International Dark Sky Park of Katahdin Woods & Waters National Monument, look for Houlton to make headlines over the next few years.
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Jonesport
While Jonesport might not be a bustling tourist hub, its unspoiled beauty and genuine maritime culture make it an underrated destination for those seeking an off-the-beaten-path adventure. This region is also among the foggiest on the Maine coastline.
From sardines to lobstering, this town has a storied past in the waters of Chandler Bay. If you’re a boater, wait until you see the islands that await, including the lesser-known Moose Peak Lighthouse on Mistake Island.
Visitors also get the bonus of Beals, a bridge-connected island that leads to the Great Wass Island Preserve, a serene 1,500-acre wilderness that boasts picturesque coastal trails.
Millinocket
Many people talk about Mount Katahdin, the end of the Appalachian Trail and the highest peak in Maine. Not enough is said about the anchor town of Millinocket in its shadow.
Hiking, camping, and wildlife-watching opportunities abound here, making it a haven for nature lovers.
The “Golden Road” to Canada is unlike any scenic drive you’ve ever seen before.
Whether you want to go deep into the Maine Woods and hike the waterfalls of Gulf Hagus or check out a few dozen others in the region, Millinocket is the headquarters for an outdoor Maine adventure.
Be sure to get a photo at Pockwockamus Rock.
Related: 10 Best Towns in the Maine Mountains to Visit This Year
New Harbor
New Harbor might technically be a village in the Downeast town of Bristol, but it holds its own underrated value.
Even romance author Nicholas Sparks couldn’t find a more idyllic place for his Message in a Bottle movie than this village.
Even the Pemaquid Point Lighthouse could square up with the Portland Head Lighthouse for amazing views and surrounding trails, including a dizzying and contrasting bedrock design for a beach.
Ferry service takes guests to Monhegan Island, and tour boats bring you face-to-face with puffins and seals. You might even see some whales.
History buffs will get two forts right next to each other.
Newry
About half of the things people love about Bethel are technically in Newry.
Sunday River Resort excels as a four-season destination. It doesn’t just offer trails and sweeping scenic views; it includes a lot of fun. The resort has events like skiing Santas and a wife-carrying contest, while Eddy and Betty (the Yetis) could show up anytime.
Two of the best swimming holes in the state are here (Frenchman’s Hole and Sunday River Swim Area).
Near Grafton Notch State Park, waterfalls await adventurous hikers, and the Appalachian Trail can lead up to the scenic view of Old Speck Mountain.
Some of the best fall foliage in the state arrives in late September, and winter roads are always plowed for easy access to the slopes.
By no means is Sunday River underrated. It has won many awards, but the town of Newry also deserves applause.
Pembroke
Many people know there’s a reversing waterfall somewhere in Maine. Or maybe they heard about it. Or is it a hoax? Reversing Falls is in Pembroke, and I assure you, video doesn’t do it justice.
The tide rises and falls up to 20 feet in this narrow stretch of water, creating a suction that makes a reverse waterfall appear. You have to time the trip just right to see it in action.
So you wanna see a moose in Maine? Head to the federally preserved land of Moosehorn National Wildlife Refuge. Cameras are planted all over the landscape, offering up-close views of moose, bears, and more birds than you can count.
Visiting Pembroke is also a great excuse to drive to Moose Island and the town of Eastport, another underrated tourism goldmine in Maine.
Phippsburg
Phippsburg is another “take up the whole peninsula” kind of Downeast town. Just head south from Bath, and a whole new Maine adventure unfolds.
The Mica Mine Trail sparkles (literally) as unmined minerals reflect the sunlight. Hike up Merritt Mountain for views that rival Camden Hills State Park while standing at the spot where Revolutionary War soldiers watched for the British on the horizon.
If you need sand in your toes, take the Morse Mountain to Seawall Beach trail.
Popham Beach State Park is not underrated by the locals. For good reason, it’s the busiest state park beach–miles of sandy shoreline and a lighthouse on the horizon. Forts Poham and Baldwin are next door.
Take the Seguin Island Ferry to the lighthouse there. All you need to do for a tour is find the caretakers and ask! While you’re there, enjoy miles of island hiking trails.
Raymond
Skip the traffic at Sebago Lake State Park and enjoy the nearby town of Raymond, which still gives easy lake access.
That the ferry to Frye Island or rent a cabin on an equally beautiful Panther Pond. You are also close to the Sabbathday Shaker Village for a unique cultural experience on the way to a much less crowded Range Pond State Park.
Maine Wildlife Park is just six miles away from your lakeside paradise.
To truly escape the crowds, head to the four miles of trails in Raymond Community Forest, with views in all directions from Pismire Mountain.
Rockwood
On the eastern edge of Moosehead Lake is Rockwood, with direct access to one of Maine’s most notable features–Mount Kineo. It has a similar appearance as Half Dome in Yosemite National Park, only no permits are required here.
Rockwood is also the last stop on the way to Maine’s North Woods, making it a perfect place to stop before going on a wilderness adventure.
You can still get all the great tastes of the Maine coast at Rockwood Bar & Grill.
While nearby Greenville at the south end of the lake is the premiere destination of Moosehead Lake, Rockwood holds its own with rustic lakeside cabins and easy walking distance to the ferry dock.
Related: A Guide to the BEST Small Towns in Maine to Visit
Stonington
Stonington offers much of the same appeal as Portland but at a much slower pace and less commercialization. For good reasons, the town has repeatedly ranked as the most underrated town in Maine.
While it’s on an island, you don’t need a boat, as the drive to Stonington is part of its appeal. It’s just 90 minutes from Bangor, and you won’t have to sit in traffic.
Once you’re there, pick your preferred path through the Island Heritage Trust or take a boat to Isle au Haut.
This working fishing village has some of the best lobster meals in Maine and a year-round Opera House with year-round entertainment for perfect date nights.
Stonington has an authentic appeal for those who love Maine; you just have to go off the beaten path to get there.
Winter Harbor
Splintered off Mount Desert Island, Winter Harbor is on the Schoodic Peninsula. This region is known as the “Quieter Side of Acadia.” It’s also the only part of the park where roads are open year-round.
Winter Harbor wraps around Henry Cove before expanding further down separate peninsulas. Grindstone Point offers epic views of the churning waves slamming into jagged bedrock.
While Winter Harbor is much smaller and less crowded than Bar Harbor across the narrows, a ferry can take you back and forth daily.
A trip here also offers quick access to more underrated communities in Maine, like Gouldsboro and Prospect Harbor.
Related: 17 BEST Coastal Towns in Maine to Visit
The Appeal of Maine’s Underrated Towns
A visitor can enjoy Maine with one trip, but you fall in love with the sum of the whole by visiting these more remote and lesser publicized places. You’ll still get the same quintessential experiences.
The number of land trusts in Maine keeps growing so Mainers and visitors like you can enjoy the preserved land without overdeveloping this beautiful natural state.
Underrated, at least in Maine, means priceless.
