Town of Wiscasset, Maine

If you drive about an hour north of Portland along winding coastal Route 1, you’ll eventually see a sign welcoming you to “The Prettiest Village in Maine,” once you pass it, you’ll know that you have, indeed, reached the pretty village of Wiscasset. The town is situated along the banks of the Sheepscot River, on one of the many fingers that jut out from the Maine coast into the mighty Atlantic Ocean, just 14 miles away.

Wiscasset is home to antique stores and art studios, restaurants and shops, and many historic buildings on hilly green slopes that overlook the harbor—one of the deepest in Maine—and the reason Wiscasett prospered through the late 18th and early 19th centuries. The village is quite a lovely place to visit and live, and whether you are just passing through or are considering relocating here, you’ll soon discover why so many people are drawn to this quaint mid-coast town.

Walking Tour to Explore Wiscasset, Maine

The best way to get to know “The Prettiest Village in Maine” is to head right downtown and embark on the self-guided tour called Wiscasset’s Museum in the Streets. Just locate and read the storyboards that have been placed around town to help you learn about the people, places, and events that helped shape Wiscasset.

The walk features Castle Tucker, the Nickels-Sortwell House, the 1811 Old County Jail, and many other historical sights and structures that make Wiscasset “one of three architecturally significant villages in the state.”

Take a Train Ride and Get the Lay of the Land

A unique way to get a feel for the lay of the land around Wiscasset is to take a train ride on the WW&F Railway, located at Sheepscot Station just 10 minutes away in Alna. The narrow-gauge railroad was built in 1894 with a dream to connect the coastal community with towns to the north—the railroad tracks never made it very far but were active serving the surrounding rural areas until 1933. The train was abandoned in 1936, and in 1989 WW&F was purchased and revived and is now one of the most exciting and interesting ways to see the scenic landscape in Sheepscot Valley.

Shopping and Eating in Wiscasset Village

After (or during) your walking tour of Wiscasset, there are many local shops and restaurants well worth visiting. We recommend grabbing a lobster roll at world-renowned Red’s Eats, in business for 83 years in the same spot—right next to the south end of Wiscasset Bridge. The lines of people that form to get Maine’s #1 lobster roll are known to create “The Biggest Traffic Jam in Maine.”

If Red’s queue is daunting, Sprague’s Lobster is nearby, also known for serving up tasty lobster rolls and steamed lobster dinners. Both these spots are seasonal, so if they aren’t open when you swing by, head over to Sarah’s Cafe for a homey dining experience. Sarah’s features burgers, sandwiches, pizzas, dinners, and yes—lobster rolls. Now, it’s time to hit the sidewalks and see the sights.

Once you’ve had your fill of historic buildings, head over to the Maine Art Gallery and catch an exhibit or pop into one of the many unique (and adorable) gift shops. There’s Moulinette and its assortment of joyful things, BIRCH with home furnishings and gifts, and for more artwork that you can view (and purchase), visit the Wiscasset Bay Gallery.

After exploring and shopping, it might be time to think about dessert, and we have just the place—Mammy’s Bakery specializes in Italian Sweet (and Savory) creations, and this is the spot to satisfy your sweet tooth! Another place to get something sweet is Creamed Baking Co..—not only can you get a freshly baked dessert, creamy ice cream, or a specialty drink; you can browse locally owned arts and crafts.

Here are a Few Interesting (and Surprising) Tidbits about Wiscasset

Wiscasset is also known as “The Worm Capital of the World” for the worms it once supplied nationally for the saltwater sport fishing industry. The Union Church in Wiscasset holds the Guinness Book of World Records for the tiniest church in the world. And check out the 1790 Tiny House—a 448 square foot home that had been in the same family for generations until recently when it was purchased and lovingly restored by its new owner—at one point, eight children were raised in this tiny home.

Then there’s the Marie Antionette connection; it’s said that there was talk of helping Marie Antionette escape when local ship captain Stephen Clough ended up in France with his vessel “Sally” during the French Revolution. The idea of Marie’s escape aboard the “Sally” was floated, and before she could be sprung from prison, the plot was discovered, and shortly after that, Antionette was beheaded.

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