An Underrated Resort Town Called Maine's 'Prettiest Village' Brims With Waterfront Dining And Shops

There's no lack of natural beauty as you wind your way up and down Maine's scenic eastern coast. As you pass through Maine's old villages seemingly paused in time, the towns meet with coastal waterways connecting to the Atlantic Ocean. A hidden gem about an hour north of the gorgeous New England city of Portland, Maine, that exudes small-town beauty in its waterfront area is the small town of Wiscasset, Maine, where the Sheepscot River splits into the Sheepscot and Back River. This village has over two centuries of New England history and infrastructure that dates back to the 19th century — including Wiscasset District Court, which has been in operation longer than any other courthouse in the U.S.

Wiscasset has both a long-standing reputation attached to its slogan of "The Prettiest Village in Maine" and a second unique nickname based on the wildlife that inhabits the area: It's reportedly the "Worm Capital of the World." However you choose to remember Wiscasset, the ambiance of the charming town itself is unforgettable, and there's so much to explore and unpack upon arrival. With a variety of antique emporiums and art galleries to explore, Wiscasset is full of quaint local shops and restaurants that make the adorable waterfront setting all the prettier. 

Though Maine residents now know the town of Wiscasset as "The Prettiest Village in Maine," there was a time when it was more popularly known as the "Worm Capital of the World." That title was given to the town by National Geographic back in 2004, referring to Wiscasset's thriving bait industry and the local popularity of summer activities like clamming and lobster fishing. While the seafood and lobster are still popular in the area, the nickname has been replaced.

The more modernly popularized slogan of "The Prettiest Village in Maine," according to Boston Magazine, comes from a statement made by famed travel photographer and writer Wallace Nutting upon visiting Wiscasset for his 1924 book "Maine Beautiful." '"Perhaps there is no other Maine village able to compete with this in the range of its attractions," he wrote. Thus, the title of "The Prettiest Village in Maine" was adopted by Wiscasset. The town center's placement in the National Register of Historic Places in 1973, paired with the sign being mounted beside Route 1, made the title for Wiscasset all but official. Today, you can journey to the town and see its historic buildings and bustling marinas and see the town's two titles coexisting.

The best memory to take from a historical destination like Wiscasset is a relic from the past; luckily, there are several antique stores in town worth a browse. The Wiscasset Antiques Mall is south of town off of Route 1 and is open seven days a week, featuring three floors full of vintage items from dealers around New England. In the heart of the town on Main Street, Rock Paper Scissors offers children's toys, handmade jewelry, and household items that could make great gifts for friends or loved ones.

Visit early 19th-century structures like Castle Tucker and Nickels-Sortwell House. Visitors need to pay for admission and for a tour. The Old Jail on Upper Federal Street is available for public viewing to see what "behind bars" looked like two centuries ago. Admission is also charged, and tours are only offered regularly between Memorial Day and Indigenous People's Day on October 13.

The town village of Wiscasset coaxes up to the waterfront and the Water Street district offers locally owned shops and cafes. Naturally, dining in Maine revolves around seafood, and visitors seeking out the best lobster rolls should stop by Wiscasset. Lobster and fresh local seafood are served at Red's Eats and Sprague's Lobster, which both come heavily recommended by visitors. Red's in particular always seems to have a long line, and if you think the traffic in Wiscasset is bad, there's a good chance the line for that lobster roll place is to blame. Dining on fresh seafood on the water is a rite of passage in Maine and a great way to start or finish a coastal town getaway. For more Maine adventures, check out our guide to the breathtaking Chebeague Island, less than an hour's drive down the coast.