The Most Charming Towns in Maine Are Even Better in Fall

Just 5 hours drive up the coast from Manhattan, Kennebunkport has become the escape of choice for city dwellers looking for a quintessential upscale New England experience. The town itself has under 5,000 year-round residents but affluent travelers (former president H.W. Bush famously spends summers here at his compound in Walker’s Point) come for the next-level restaurants, luxury lodging and art galleries. Don’t miss the Seashore Trolley Museum -- the largest and oldest one of its kind in the world -- and Dock Square, the town’s epicenter for gallery hopping, shopping and dining.

Located in Mid Coast Maine just south of Camden, is the picturesque harbor town of Rockland. For art lovers, stroll over to the Farnsworth Art Museum, which houses more than 15,000 works by American artists including the largest collection of pieces by the Wyeth family, or check out  the smaller local galleries. An absolute must for foodies is the restaurant Primo, the town’s champion of farm-to-table cuisine by James Beard award-winning chef Melissa Kelly.

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Many will recognize Bar Harbor as the gateway to New England’s only national park, Acadia, but beyond being an ideal base for exploring the area’s natural delights, Bar Harbor has plenty of charm unto itself. As the largest town on Mt. Desert Island (with a whopping 5,000 residents), Bar Harbor (or Bah-Ha-Bah as it’s pronounced by locals) is where you’ll find that true Down East spirit. Don’t miss a sunrise stroll along the ½ mile long Shore Path that looks out over the Porcupine Islands, or plan a visit to Bar Island at low tide when you can walk across the sand bar for a stunning view of Bar Harbor’s bay, with the Acadia as the backdrop.

A more convenient trip for those traveling North is Ogunquit, which sits just 16 miles past the New Hampshire border. What was once a small fishing village is now the go-to summer retreat for travelers who prefer soft, sandy beaches to the rocky stretches that characterize many other coastal Maine towns. The town's highlights: the Marginal Way coastal cliff walk, which will help burn off all the lobster rolls you’re sure to consume during your visit, and an evening show at the Ogunquit Playhouse. 

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For travelers looking to get out on the water, Boothbay Harbor is the place to do it -- whether that’s on one of the area’s whale watching adventures, sailing tours or kayaking excursions. For the seasick-prone, there’s plenty to do on land including dining at the many waterfront restaurants--we love the Lobster Wharf--or exploring the one-off shops lining Main Street. For a special treat, head over to Downeast Candies, which has been making salt water taffy since 1974. 

When it comes to iconic Maine, Camden is the cream of the coastal crop. The picturesque harbor has been reimagined for many a landscape painting and the 100-year-old Camden Yacht Club is still the town's main institution, where well-heeled families reunite during the summer months. Spends your days on the water--on a windjammer, dingy or kayak--and make sure to visit Mount Battie for the best views of coast.

Home to the famous Red Eat’s lobster shack, Wiscasset is so much more than a food pit-stop along the way to Maine’s Mid Coast. The town seems eager to prove its worth with a sign easily witnessed by all passersby along Route 1 that declares: “the prettiest village in Maine.” It’s hard to contest the declaration when you have a town like Wiscasset, which is filled with historic architecture and has a picture-perfect coastline. Leave plenty of time to explore the town's antique shops and to visit the smallest church in the world. 

Michelle is the travel writer, photographer and wanderer behind the site Livelikeitstheweekend.com. She has spent the last two years on the road working from a laptop and exploring some of the most beautiful places around the globe. You can see her travel highlights over on her Instagram @Livelikeitsthewknd