The Most Picturesque Towns In Maine

The towns on this list take their superlatives seriously. Millinocket sits at the doorstep to Maine's tallest peak and largest state park, with unlimited options for exploring Mount Katahdin in all its glory. Stonington hauls in the most lobster by the pound of any seaport in the state. Bar Harbor and Ellsworth are gateways to Maine's only national park. Their claims to fame are what make these towns spectacular. Think colorful boats bobbing in the harbor, fiery fall foliage, and picture-perfect small town streets set against a quintessential New England backdrop. When the itinerary calls for a vacation as picturesque as it is relaxing and rejuvenating, Maine has just the spot.

Bar Harbor

Located on Mount Desert Island, which also holds Acadia National Park, Bar Harbor is a walkable, friendly waterfront town. Downtown, you'll find streets full of restaurants and locally owned shops. Sherman's Maine Coast Book Shop is a must-visit for book lovers, and if you have four-legged best friends, definitely wander into Bark Harbor for a lobster squeaky toy or Maine-themed accessory for Fido. Waterfront restaurants are also in high demand, and rightly so. Hot spots include The Terrace Grille, The Chart Room Restaurant, and the Reading Room at the Bar Harbor Inn. Many restaurants in Bar Harbor are only open seasonally, however, so be sure to check hours before you go.

Freeport

A giant L.L. Bean boot marks the retailer's headquarters in Freeport, though the town has more going on than its most famous storefront. Downtown Freeport is walkable and full of shops housed in historic buildings, some of which date back to the 1800s. Visitors can browse the Rustic Arrow and the Mangy Moose in the village, or drive a mile north to Maine Wicked Goods Mercantile, an antiques and art shop in a red building on Route 1. Freeport Village Station anchors the outlet shopping in the middle of town. Of course, a visit to Freeport isn't complete without a stop by Maine Beer Company for an ale and a wood-fired pizza, or a run down to Harraseeket Lunch and Lobster on the pier in South Freeport for a fresh-off-the-boat lobster roll.

Millinocket

The gateway to Mount Katahdin, Maine's highest mountain at 5,269 feet, Millinocket is a scenic town in the state's North Woods. Maine's Biggest Small Town, as it's called, is the state's headquarters for outdoor recreation of all varieties, including hiking, whitewater rafting, snowmobiling, and skiing. For a laid-back visit to the North Woods, book a cabin at Ktaadn Resorts, the lakeside adventure resort formerly known as the New England Outdoor Center.

If you're keen to get out on the water, there are accommodations at Northern Outdoors' Katahdin Adventure Base Camp. Both spots have easy access to Katahdin and to Baxter State Park, Maine's largest state park at more than 200,000 acres. There's plenty to do in town, too. Scootic In Restaurant has been serving Millinocket since the Simon family opened it in the early 1900s, making it the oldest restaurant in the area, and its menu draws steady praise. Gather Inn offers cozy accommodations for guests in a 1900s colonial.

Ellsworth

Located a short drive from Mount Desert Island and Bangor, Ellsworth is often hailed as the Gateway to Acadia, and this community of roughly 8,400 has a Mayberry kind of energy. Its downtown is an official Main Street Maine community and holds lots of shops and small businesses, as well as restaurants and small grocery stores. Old Creamery Antique Mall is a must for vintage finds, and bibliophiles will be in heaven perusing Big Chicken Barn's 21,000 square feet of books and antiques in, as its name suggests, a former chicken barn.

Discerning diners enjoy spots like Conscious Cafe Ellsworth, a weekday lunch counter working out of the Steamy Buddha kitchen on Church Street, plus Airline Brewing Company Pub and Provender Kitchen + Bar. If you're planning on staying in Ellsworth, The Sanctuary Inn and Art Gallery is a converted building that hangs local work in its common rooms and rents studio space, and it's a short walk from downtown.

Stonington

Sitting at the southern tip of Deer Isle, Stonington is a tiny town of about 1,000 linked to the mainland by bridges and also accessible via watercraft. Isle au Haut Boat Services runs out of the town landing to Isle au Haut, where summertime passengers can get off at the Duck Harbor stop inside Acadia National Park.

In a state known for lobster, Stonington is superlative. More lobster, measured in pounds, is landed here than at any other Maine port, and the fleet runs to more than 300 boats. The town is known for its waterfront vistas and seafood restaurants, and Stonecutters Kitchen sits right across from the dock with chowders, stews, and a dining room looking out on the working harbor. A few doors along, Opera House Arts programs films, concerts, and theater inside the Stonington Opera House, built in 1912 and since restored.

Monmouth

Monmouth is a small town of roughly 4,000 in Kennebec County, sitting between Lewiston-Auburn and Augusta. It is known as one of the best agricultural towns in Maine and produces hay and apples, so when you visit Monmouth, expect quiet rural scenery and nods to the area's history. Settled in the 1770s, the town went by several names before it was incorporated as Monmouth in 1792. The name came from Henry Dearborn, a landowner and Revolutionary War officer who fought at the Battle of Monmouth in June 1778.

As you explore the town, you'll pass historic buildings like Cumston Hall, whose stained glass is especially good at sunset. Listed on the National Register of Historic Places in 1973, Cumston Hall is one of the most flamboyant examples of wooden Romanesque Revival architecture in a small-town setting anywhere in the state. It was designed by the muralist Harry Hayman Cochrane and given to the town by Dr. Charles M. Cumston, and it still houses the Cumston Public Library along with an auditorium where the Theater at Monmouth performs.

Ogunquit

A small coastal town on Maine's south shore, Ogunquit takes its name from the Abenaki, commonly translated as "beautiful place by the sea." The town's quiet coastal beauty has made it a popular tourist destination, and its population of 1,600 booms during the summer travel season. Today, the four-square-mile town of Ogunquit is defined by its soft sand beaches, robust arts and theater scene, warm and welcoming LGBTQ+ community, and abundance of independently owned dining, shopping, and accommodation options. Ogunquit Beach is a popular spot for sunbathing, and Perkins Cove features a bevy of businesses, art galleries, and dining options. If you're into the arts, definitely check out a show at Ogunquit Playhouse, a regional theatre offering large-scale Broadway-style shows in the summer and fall.

Kennebunkport

If you're looking for a quintessential Maine coastal town, it's Kennebunkport. This town of 3,600 on Maine's southern shores has beaches at both ends of its coastline. Goose Rocks runs three miles of soft sand on the northeast side, while Colony Beach sits at the mouth of the Kennebunk River, small and sheltered behind a rock jetty that people fish off all summer. Both make it a favorite place for family vacations. It's worth noting that beach wheelchairs are available for public use in the Kennebunks, making this coastal locale especially accessible.

No visit to Kennebunkport is complete without a stop at The Clam Shack, where patrons can enjoy a lobster roll and a Coke while strolling along the Kennebunk River. Or, if you're looking for a more fine dining experience, The Boathouse boasts beautiful views and an elevated "Classic Maine" menu full of fresh, seafood-forward dishes.

Choosing Between Them

Each of these towns has something to offer on a scale of cute to stunning, so making a choice really comes down to seasonal preference and aesthetic. In the northeast, winter can be tricky for travel, and some businesses may be closed or have limited hours, but the payoff is having the place largely to yourself without the tour buses and summer crowds. In the warmer months, there's an air of festivity and a buzz around the waterfronts that make these places popular. No matter the season, Maine puts on a beautiful show, especially in these stunning towns.