13 Charming Small Towns in Maine

The renowned gateway to Acadia National Park, Bar Harbor is a splendid seaside village with tons of outdoor adventure and gorgeous views at every turn. None more spectacular than the vistas from Cadillac Mountain over to the bay and the Cranberry Islands. (Pro tip: Hit the trails in the wee hours of the morning and reap the sunrise rewards.) Set aside some time for the scenic Shore Path, which starts at the town pier and runs along the eastern shore of Mount Desert Island.

Where to stay:

• Bar Harbor Motel (2 guests): $99/night
• Saltair Inn Waterfront B&B (2 guests): $188/night
• Ivy Manor Inn - Village Center (2 guests): $199/night

Of all the adorable and atmospheric towns in the Pine Tree State, Kennebunkport might be the one that gets the most press. And, honestly, it’s not a case of good PR but rather just an exceptional destination that very much deserves the praise that’s heaped atop of its award-winning restaurants, independently owned shops selling all sorts of local goodies, lively bars and quaint inns. The coastal walk to the Bush family compound and vacation home is quintessential Maine.

Where to stay:

• Kennebunkport Inn (2 guests): $189/night
• The Boathouse Waterfront Hotel (2 guests): $209/night
• Yachtsman Lodge & Marina (2 guests): $269/night

Lobster shacks and sandy beaches have come to define Ogunquit. Honestly, those are two pretty awesome (and accurate) drawcards. This picturesque little town on Maine’s southern coast also has a slew of terrific art galleries and an idyllic cliff walk called Marginal Way. Plus, the Ogunquit Playhouse stages theater productions in the summer months. Curious about public transport? It’s an old-fashioned trolley. Because Ogunquit is just that delightful.

Where to stay:

• Sea Rose Suites (2 guests): $89/night
• Gorges Grant Hotel (2 guests): $104/night
• The Dunes on the Waterfront (2 guests): $140/night

Wells may be the third oldest town in Maine (it was established back in 1641 and named after the city of Wells in Somerset, England) but we wouldn’t dare put it in the bronze position in any other category. This darling gem with a population of just over 9,000 friendly residents turns on the charm with its historic attractions such as Wells Reserve at Laudholm and barrier beaches. For even more natural beauty, head to the Rachel Carson National Wildlife Refuge.

Where to stay:

• Wells - Ogunquit Resort Motel & Cottages (2 guests): $86/night
• Elmwood Resort Hotel (2 guests): $129/night
• Ogunquit River Inn an Ascend Hotel Collection Member (2 guests): $129/night

When in Boothbay Harbor (for clarity, we mean both the classic Maine town and its namesake waterfront) it's a must to rent a kayak or book a sailing lesson. Prefer to stay on dry land? There are lots of specialty shops, bars and seafood eateries. And it’s not uncommon to lose track of time just meandering around and marveling at the traditional white clapboard houses. Obviously, you’ll want to cross the Boothbay Footbridge.

Where to stay:

• Brown's Wharf Inn (2 guests): $195/night
• Boothbay Harbor Oceanside Golf Resort (2 guests): $216/night
• Topside Inn (2 guests): $259/night

You’ll often hear Camden described as the “Jewel of the Coast.” That’s certainly true. It could also be called Maine’s movie set on account of its popularity as a filming location. It’s easy to see why Hollywood loves this postcard-pretty seaport. Camden cuts quite the impression with its harbor full of sailboats, amphitheatre, public library and historic, ocean-view mansions. An abundance of outdoor activities—from hiking in Camden Hills State Park to winter sports—and festivals make it a great year-round destination.

Where to stay:

• Hartstone Inn & Hideaway (2 guests): $179/night
• 16 Bay View (2 guests): $197/night
• Grand Harbor Inn (2 guests): $233/night

Seafood lovers rejoice! Every foodie knows the first stop in Wiscasset is always Red’s Eats, a family-run institution that consistently earns praise from chefs and hungry travelers alike for its award-winning lobster rolls. (Don’t sleep on the crab cakes either.) Besides great grub, Wiscasset has many historic landmarks such as the Federal-style Nickels-Sortwell House and Castle Tucker, a historic mansion that’s set on a hill overlooking the Sheepscot River. Wiscasset can brag about being home to the smallest church in the world.

Where to stay:

• Lovely Studio (2 guests): $79
• 13-Acre Property on the Sheepscot River (6 guests): $317/night
• Waterfront New England Charmer (8 guests): $225/night

You don’t need to be a history buff to appreciate the heritage-rich town of Castine. One of the oldest settlements in North America, this long-standing community situated on a peninsula in Penobscot Bay is packed with tell-tale New England architecture (think: white clapboard houses with American flags that flap in the salty sea breeze), churches, antique shops and twee inns. Folks with an interest in the past, should def swing by the Castine Historical Society.

Where to stay:

• Downtown Studio (2 guests): $135/night
• In-Town Bungalow (6 guests): $143/night
• Oceanfront Home Overlooking Penobscot Bay (8 guests): $375/night

With a prime perch beside the Atlantic Ocean on the Gulf of Maine, York—which, for anyone keeping score, is the second oldest town in the state—has long been a popular summer escape for travellers up and down the Eastern Seaboard. It boasts beautiful beaches, tons of family-friendly activities (what kid doesn’t like putt-putt?) and the endlessly photogenic Nubble Lighthouse. You can gobble up fried seafood, lobster rolls and clam chowder. While salt water taffy sweetens the deal.

Where to stay:

• Lighthouse Inn and Carriage House (2 guests): $99/night
• Inn at Tanglewood Hall (2 guests): $220/night
• Stage Neck Inn (2 guests): $250/night

A longtime hidden gem turned popular tourist destination, the seaside village Rockport, which sits between Rockland and Camden, retains its low-key ambiance. There’s just way more fun stuff to do. Activities run the gamut from boating and exploring Beech Hill Preserve’s hiking trails to mini golf and gallery hopping. And who could possibly pass up the chance to moo it up with Belted Galloway cows at Aldermere Farms? Not us, that’s for sure.

Where to stay:

• 1990 Refurbished Barn (3 guests): $225/night
• Artistically-Inspired Home (4 guests): $200/night
• Antique Farmhouse (6 guests): $185/night

Located five miles southeast of Portland, Cape Elizabeth really does tick all boxes of a great seaside getaway. With a mix of craggy coastline and sandy beaches, you get all the coastal Maine beauty you’d see on postcards in one fell swoop. Fort Williams Park is well known for its arboretum, cliffside loop and scenic picnic areas. Don’t miss the chance to visit Portland Head Light, the oldest lighthouse in the entire state.

Where to stay:

• Apartment Near Crescent Beach State Park (3 guests): $251/night
• Newly Built Cottage (7 guests): $495/night
• Oceanfront Cottage (6 guests): $571/night

Seven miles of beach to spread out your towel and relax may be the main (or, shall we say, Maine) claim to fame of Old Orchard Beach but it’s far from the only selling point. Located right on Saco Bay, this lovely town deserves to be more than just a day trip from Portland. Savor fresh seafood, take a nostalgic ride on the Tilt-A-Whirl at Palace Playland Amusement Park, go kayaking and hit the links at Pirate’s Cove.

Where to stay:

• Old Orchard Beach Apartment (2 guests): $110/night
• Oceanfront Condo (4 guests): $115/night
• Beachfront Victorian Condo (6 guests): $198/night

Damariscotta is a bit of an unsung hero on the Pine Tree State tourism circuit. For the life of us, we can’t figure out why. Our guess would be the location. It’s about 20 miles upriver from the open ocean. We certainly don’t mind having more room to peruse the excellent selection of titles at Maine Coast Book Shop and Cafe, gallery hopping sans hordes of art aficionados or the ease of nabbing tickets to the Lincoln County Community Theater.

Where to stay:

• Condo in Town (2 guests): $108/night
• Midcoast Maine Condominium (3 guests): $115/night
• The Gallery Apartment (3 guests): $115/night