14 Prettiest Towns In Maine
Hidden in the far northeastern corner of the United States, Maine showcases the charm of the rugged eastern coastline and is home to some of the prettiest towns in mainland America. Nicknamed “Vacationland,” Maine draws 25 million visitors each year. The slower pace of life here is sure to entice you to relax and reset during your visit. If lighthouses, lobster feasts, rocky walks along the shore, and historic charm ring your bell, then consider Maine for your next fair-weather getaway.
Boothbay Harbor
The mid-coast peninsula town of Boothbay Harbor claims “one of the best boating harbors” north of Boston. Attracting sea captains, fishermen, and marine biologists, this fetching seaside town is home to nature lovers and artists who can’t get enough of that salty sea air. For a once-in-a-lifetime experience that will give you a new appreciation for coastal Maine, try a two-hour sailing trip aboard a tall ship with Schooner Eastwind or Schooner Applejack. The perspective from the water is second to none.
Famous for its lobster fishing, Boothbay Harbor provides several ways to enjoy this classic east coast delicacy. Consider visiting the Boothbay Lobster Wharf for a rustic seaside snack or a deep-fried treat with steamed corn on the cob. Reflecting New England’s rich history, a quick 13-mile drive inland will take you to Castle Tucker, built in 1807. Open from June to mid-October, its interior feels as if frozen in Victorian times, offering a nostalgic glimpse into its past as a historic family home.
Ogunquit
With its beautiful beaches, Ogunquit lives up to its name, which means “beautiful place by the sea” in Abenaki, a Native American language. This southern Maine destination is perfect for relaxing on long summer days. Park your car and take a walk along the Marginal Way, a 1.25-mile trail with gentle slopes offering stunning ocean views. While Ogunquit Beach can be crowded with swimmers, if you prefer quieter moments, head toward the fishing village of Perkins Cove. There, you can enjoy a meal, browse boutique shops and art galleries, or watch fishermen bringing in their daily catch.
York
Just south of Ogunquit along the coast, you’ll find York. Known as America’s first chartered city in 1641, York was named after Yorkshire, England. A major attraction here is the historic Cape Neddick Light Station, popularly called Nubble Lighthouse. Built in 1879, the last lightkeeper and his family moved out in 1987 when modern technology made it fully automated. Today, the town of York is the permanent keeper of the lighthouse, maintained by the Parks Department. York also hosts one of the oldest prison buildings in the U.S., Old York Gaol, built in 1720. The single stone cell block’s walls are 2.5 feet thick. Visitors can take a step back in time with a tour of this wood-framed structure from May to October. After exploring history, it might be time to enjoy a round or two of golf at one of the area’s three beautiful 18-hole courses.
Stonington
For a fishing port vibe, Stonington, Maine, is ideal. Like many charming towns along the Atlantic coast, it offers a vibrant glimpse of east coast life. Situated at the southern tip of Deer Isle, fishing clearly dominates as the main industry and lifestyle. When not looking out to sea, you'll notice the 19th-century architecture lining the winding inland roads. However, the highlight is the seashore, which continually attracts visitors like a siren’s call. If you love seafood and fresh salt air, this spot serves as a perfect gateway to the Merchant’s Row archipelago.
Damariscotta
Slightly further inland along the Damariscotta River is the town of Damariscotta. Once inhabited by indigenous Abenaki peoples, the river provides an abundance of edible marine life, including horseshoe crabs, river herring, oysters, and mussels. When Europeans settled here, Damariscotta grew into a hub for shipyards and brickyards that served—and built—the city of Boston. Today, the area is popular with outdoor enthusiasts for kayaking, hiking the scenic trails, biking, or taking a river cruise. For indoor lovers, there’s the historic Lincoln Theater, various art galleries, museums, and shops. For dining, enjoy a wide variety of seafood and other options that rival big-city restaurants.
Camden
Camden is an absolute stunner located on Penobscot Bay in Maine’s mid-coast region. Its coastal New England charm will have you wishing you lived here year-round. The autumn and winter landscape scenes are picture perfect. And the Camden Snow Bowl is the only ski resort on the east coast with a view of the ocean. Aside from its endless outdoor activities, Camden enjoys a rich history. Though the downtown was ravaged by fire in 1892, it came back stronger with beautiful brick architecture that remains a testament to this harbor town’s enduring nature. Hollywood location managers love it for a nostalgic backdrop to movies like Casper and TV shows like Peyton Place.
Greenville
Lake lovers, dust off your canoes! The farthest inland on our list of prettiest towns in Maine, Greenville hugs the shore of Moosehead Lake, the largest body of fresh water in The Pine Tree State. Hop aboard the Katahdin steamboat for a scenic tour or aim higher with one of Jack's Air Service seaplanes. For those who prefer to go under their own steam, rental options include kayaks, SUPs, or canoes. If you're interested in fishing, rent a boat or join a fishing charter. Land enthusiasts can explore the hiking trails on Big Moose Mountain. If moose-spotting is on your bucket list, be sure to sign up for a guided tour, where you might see a 2,000-lb rubber-nosed swamp donkey in the water or on land. Fun fact: Moose calves can outrun a human by the time they are five days old.
Rockland
Strap on your lobster bib and join Rockland’s annual Lobsterfest! This five-day event draws crustacean-loving visitors from all over the US and beyond. Protected by Rockland Harbor, this pretty little town is marine magic at its finest. Dotted with sailboats, fishing boats, and even tall ships, the harbor’s rocky shore is a place to sit and contemplate life. Limestone and granite quarries have provided the building blocks of this town’s landmark structures and many others in the state. The breakwater was constructed with 700,000 tons of Rockland granite blocks. Take a daytrip to one of the gorgeous islands in and around Penobscot Bay.
Castine
Another pretty town on Penobscot Bay is the one-time trading post of Castine with a population of less than 1,500 folks. Home to the Maine Maritime Academy, graduates become mariners and engineers following their world-class hands-on training. Castine’s sloping main street will take you directly into the water but be sure to stop into the boutiques and eateries along the way. If you’re ready to take to the water, consider a kayak excursion with Castine Kayak Adventures. The calm waters of the bay let you cruise at your own pace. Aside from the view of the bay, Castine boasts a deep history and classic New England architecture along elm-lined streets. Homes, town buildings, and churches all offer a cozy feeling of yesteryear.
Old Orchard Beach
The popular seaside resort town of Old Orchard Beach sits on Saco Bay. In the summer, sunbathers (and their umbrellas) dot the beach in every direction. The oceanside amusement park, Palace Playland, is home to the first carousel in the United States. This seasonal attraction is one of the reasons the beach plays centerstage among travelers. The pier is another. First made of steel in 1898, The Pier was the longest of its kind (1,825 feet) and constructed by the Berlin Iron Bridge Co. at a cost of $38,000. Once iconic, the pier’s casino hosted the likes of Guy Lombardo, Louis Armstrong, and Frank Sinatra. But tragedy devastated the structure more than once and today the wooden Pier stretches only 500 feet and offers carnival-style food shacks, souvenir shops, and The Pier Patio Pub that features live entertainment four nights a week. Sunset on the beach is not to be missed.
Waldoboro
You might be asking yourself “Where’s Waldoboro?” Mid-coastal between Rockland and Damariscotta in Lincoln County, you’ll find the once German settlement of Waldoboro, named after American merchant Samuel Waldo. On the banks of the Medomak River, this agricultural hub is enjoying a renewed interest in traditional agrarian arts, like cheesemaking, soapmaking, fermentation, and others. A toy collector’s haven, check out Fawcett's Antique Toy and Art Museum. The world-class antique displays will take you to a simpler time as your eyes playfully dance through stacks of artifacts. And you can stay in the reverie of old-world charm when you visit Odd Alewives Farm Brewery, a newly renovated 1820s barn that’s home to the brewery and tasting room. Locally sourced ingredients for all the drinks and eats give visitors a real down-home taste of rural Maine.
Kennebunkport
One of the oldest European-settled towns in the US, this popular New England destination is not only fun to say, but also to visit! A famous summer getaway spot for the late President George H. W. Bush and his son President George W. Bush, Kennebunkport, Maine also attracts regular folk and world travelers alike. Though you can’t visit the Bush’s waterfront Walker’s Point estate, you can catch a glimpse of it from a distance at Blowing Cave Park on Ocean Avenue. A better use of your visit might be spent in the historic district of the Lower Village. A peaceful, pretty town with friendly residents, a trip to Kennebunkport is a perfect escape from the hustle and bustle of everyday life. Both the ocean port and Kennebunk River have shaped this town’s shipping and fishing history. Beach lovers will definitely want to take in the flat, soft, sandy Goose Rocks Beach for sunbathing, walking, jogging, or just relaxing the afternoon away. Like most coastal towns, Kennebunkport attracts artists who are inspired by the magnetism of the water. For travelers this means artwork abounds in galleries and boutiques that invite you to take a treasure home.
Bar Harbor
Adjacent to Acadia National Park on Mt Desert Island lies Bar Harbor (locally pronounced Bah Hahbah). This charming coastal town is flanked by rolling mountains, with Cadillac Mountain as the highest at 1,530 ft. Drive up to the summit to enjoy stunning views of the Atlantic and rugged shoreline. The Cadillac Summit Loop Trail attracts many visitors, so if you seek solitude, it might not be the best choice. At sea level, visitors can explore Bar Harbor Ghost Walks, Pirate’s Cove Adventure Golf, Coastal Kayaking Tours, and lighthouse boat cruises. The town also offers a shopping paradise with local art, specialty foods, gifts, and more. For dining, fresh seafood caught straight from the boat is hard to beat. Try Paddy’s Irish Pub & Restaurant at the West Street Hotel or enjoy authentic Italian at Mama DiMatteo’s, where there’s “no such thing as too much garlic.” Bar Harbor serves delicious options to suit every taste. As evening falls, catch breathtaking sunsets from spots like the Town Pier, Agamont Park, the Bar Harbor Sand Bar, or from a scenic sunset cruise.
Swan’s Island
The tiny island town of Swan’s Island is a sanctuary of outdoor adventure. Explore fine sandy beaches in search of beach glass and other jewels from the sea or ramble along the rocky outcroppings of the island. Swimmers can take a dip in the quarry pond for a peaceful experience or the sea for a less predictable one. Be sure to visit the historic Burnt Coat Harbor Light Station. Hiking the island trails is one way to enjoy the stunning scenery of this calm coastal town. Joining a sightseeing charter is another way. The friendly, welcoming islanders will add to your visit of this sweet little town, where spectacular food, relaxation, and stunning sunsets are unforgettable.
Maine was the 23rd state to join the union in 1820. With its long New England history, it captivates the hearts of visitors and locals alike. Explore this unique state where rugged shorelines embrace the ocean, inviting hiking, exploring, and breathtaking sunrises. Meander through scenic fishing villages, where lobster shacks and historic architecture create an enchanting ambiance. Enjoy warm hospitality as you savor succulent lobster feasts, indulge in artisanal craftsmanship, and sail along pristine waterways. A visit to Maine promises an idyllic escape into a world of timeless beauty and genuine tranquility that keeps calling you back.
