The Best Small Towns in Maine

Whether you’re planning a well-deserved honeymoon, long-overdue family vacation, or spontaneous New England getaway, you won’t find a more perfect destination than Midcoast Maine. Not only does our particularly beautiful stretch of the East Coast provide travelers with world-class seafood, unforgettable sailing adventures, and the prettiest lighthouses, but you’ll also discover some of the most charming, historic small towns in America. In fact, many of the best small towns in Maine are within an hour from Newagen Seaside Inn, making our oceanfront property an ideal location for an escape.

The 3 Best Small Towns in Maine near Newagen

To ensure that your summer or fall getaway to Newagen Seaside Inn is nothing short of flawless, we’ve compiled three of our favorite small towns in Maine. All of these picturesque communities offer travelers delicious seafood, historic downtowns, and charming nautical appeal.


best small towns in maineEighteen miles north of Newagen Seaside Inn is perhaps the prettiest village in New England: Wiscasset. There are several reasons that Wiscasset has blossomed into one of the best small towns in Maine, most notably the Sheepscot River views and world-renowned lobster rolls. Here are three unique reasons to visit Wiscasset:

  1. The lobster rolls: Wiscasset is known for its lobster shanties, particularly Red’s Eats, the “World’s Best Lobster Shack” and Andrew Zimmern favorite. Sarah’s Cafe, Sea Basket, and Sprague’s Lobster also feature succulent Maine lobster rolls.
  2. The history: Go back in time with a full day of engrossing museums, historical homes, and tiny churches. A trip to Wiscasset is incomplete without a visit to Castle Tucker, the Nickels-Sortwell House, the Smallest Church in the World, or the 1812 Jail.
  3. The Sheepscot River: Unlike many of the other best small towns in Maine, Wiscasset is located on a serene river, not a bay. The Sheepscot River is lovely during autumn’s peak as the valley transforms into a colorful mixture of crimson, burnt orange, kelly green, and marigold.

Boothbay Harbor

While we’re technically located in Southport, Boothbay Harbor still feels like home. This popular, harbor city is the headquarters for sailing enthusiasts, adventurers, and foodies. Boothbay Harbor is beautiful, convenient, and home to some of the top things to do in Maine, including whale watching, sailing, and hiking. Here are three reasons to visit one of the best small towns in Maine, Boothbay Harbor:

  1. The cruises: Choose between Cap’n Fish’s Whale Watch, Balmy Days Cruises, and the Schooner Eastwind for a mid-day adventure. Whether you’re hoping to spot migrating whales, learn to sail, or cruise past towering lighthouses, you’ll never forget your day at sea.
  2. Cabbage Island Clambakes: Hop aboard the famous Bennie Alice in Boothbay Harbor’s pier en route to Cabbage Island, where you’ll be treated to a quintessential New England clambake. Savor fish chowder, steamers, corn on the cob, blueberry cake, and, of course, Maine lobster.
  3. The Opera House: Nearly every night of the week, the Opera House at Boothbay Harbor presents live music. This 125-year-old establishment hosts over 100 events annually, so you’re bound to catch a rousing regional act.


Damariscotta, which is located across the Damariscotta River from Newcastle, is a scenic, 21-mile drive from Newagen Seaside Inn. This charming riverfront village is known for its tasty New England fare, eclectic shopping, and easy water access. Here are three reasons to include Damariscotta in your daily itinerary:

  1. The food: Damariscotta offers travelers (especially foodies) a “True Taste of Maine.” We highly recommend Damariscotta River Grill’s farm-raised Scottish salmon, Larson’s Lunch Box lobster roll, and the seafood pot pie at King Eider’s Pub.
  2. The shopping: Downtown Damariscotta is home to dozens of local businesses that thrive during spring, summer, and fall. Some of the best shops along Main Street include Sherman’s, Reny’s, Sheepscot River Pottery, and Stars Fine Jewelry.
  3. The kayaking: Midcoast Kayak provides adventurers with a wide variety of paddling tours along the Damariscotta River as well as Muscongus Bay. You can also rent a kayak if you’re aiming to venture onto the river with nothing but a map and a thirst for exploration.

Oceanfront Hotels in Maine

best small towns in maineAfter a full day of exploration, taste-testing, and shopping in some of the best small towns in Maine, return to Newagen Seaside Inn for dinner at The Pub and drinks at dusk, or cruise along in one of our cruiser bicycles. We’re nestled among the pines located along the Atlantic Ocean’s edge, overlooking beautiful Cape Harbor. You won’t find a more desirable after-dinner locale in Maine to relax, unwind, and recharge. Call us today at 207-633-5242, or visit our website to book a well-deserved vacation to Newagen Seaside Inn near Boothbay Harbor, one of the most beautiful coastal towns in Maine.