This Tiny Town In Maine Boasts Old-School Charm And Drool-Worthy Lobster Rolls

Wiscasset is a charming historic town along the waterfront of Midcoast Maine, and it's where you'll find some of the most delicious lobster rolls in all of New England. But you should probably plan a road trip to taste them for yourself.

Wiscasset sits along the Sheepscot River, an estuary that fills with sea water during high tides. It was first settled in 1660, but the village was abandoned when the French and Indian Wars, as well as King Phillip's War, took place in the mid-18th century. When the village was eventually resettled, it received the name Pownalborough, but this didn't stick. Its original name, Wiscasset, which roughly means "coming from the water, but you don't see where" in Abenaki, was restored in 1802. Wiscasset then grew into the largest shipping port north of Boston. Though its prominence didn't last, its Federalist-style architecture certainly did. The Wiscasset Historic District is now on the National Register of Historic Places.

In 2023, the town was home to just under 4,000 people (via Town of Wiscasset). For those interested in visiting, U.S. Route 1, a scenic highway where you can catch some of the most breathtaking views in New England, runs right through the town's center. It's also an easy, one-hour drive north of Portland, which is one of the underrated cities in the Northern U.S. you shouldn't skip visiting. The Portland International Jetport (PWM) receives nonstop flights from many East Coast cities.

The Wiscasset Historic District looks much like it did when it was built in the 18th and 19th centuries. Unlike other historic villages along Maine's coast, the buildings in Wiscasset didn't need much restoration, though you will find historical markers all over town.

As you drive into Wiscasset on U.S. Route 1, you'll pass the Lincoln County Courthouse, a brick building constructed in 1824. It's now the oldest courthouse in New England still in operation. Farther down the road is the Sunken Garden, a public garden created in the former cellar of a hotel that burned down in 1903, as well as the Nickels-Sortwell House, an 1807 captain's mansion. Just a few blocks from the highway sit the Ancient Burying Ground, where gravesites were first dug in 1735; the Lincoln County Museum and 1811 Old Jail; and Castle Tucker, an 1807 hilltop mansion.

Along the Wiscasset waterfront, you'll find antique stores, art galleries, and small shops tucked into historic buildings. The Wiscasset Antiques Center has pieces dating as far back as the American Revolution. Red Bull Antiques, set in a restored barn, sells heirloom furniture. A historic schoolhouse is now the seasonal Maine Art Gallery, which showcases local artists. Moulinette and Rock Paper Scissors are among the shops you can pop into while walking through town, while TREATS will satisfy any sweet tooth with its homemade baked goods.

No trip to Wiscasset would be complete without trying at least one of the town's famous lobster rolls. Two of Maine's most famous places to get this signature dish, Red's Eats and Sprague's Lobster, are right across the street from one another. Both are seasonal takeout spots with lines extending down the road toward the Sheepscot River. Red's Eats, which we think is one of the best places in Maine for a lobster roll, has been open for more than 80 years. It has also been featured on countless TV shows and won numerous awards. It shucks and serves almost 15 tons of lobster meat each season. Customers get to choose whether they want their lobster roll with a side of butter or mayonnaise.

Sprague's Lobster isn't quite as old as Red's Eats, but the family-owned lobster shack has still been open for 50 years. The kitschy eatery has plenty of nautical decor outside, like lobster traps and carved fishermen statues. It also has wooden picnic tables and jazz music. Like its nearby rival, Sprague's Lobster serves big lobster rolls. Each comes on a split-top bun that has been buttered and toasted. The restaurant also offers full lobster dinners, complete with a whole lobster, steamed clams, corn on the cob, and coleslaw. With such tasty local fare, it's easy to see how Wiscasset has captured the hearts of both history lovers and foodies.