Nestled along the Sheepscot River between Bath and Damariscotta, Wiscasset’s charm is thanks in large part to its historic architecture and picturesque waterfront. However, there’s far more to discover when a local is guiding you. We spoke with Debbie Gagnon, co-owner, president, and general manager of lobster roll destination Red’s Eats, to get her tips for visiting her hometown.

Main Street Staples

No matter how long you plan to stay, a trip to Wiscasset is incomplete without stopping in at the shops along Main Street. Red’s Eats co-owner Debbie Gagnon recommends visiting boutiques In the Clover, which specializes in body and skin care products, clothing, and unique accessories, Moulinette, where she goes when she needs to buy a gift for the children in her family, and Rock Paper Scissors, where owner Erika Soule and her dog, Lucy, are known to greet customers and chat while they browse the wares. “It’s important that visitors take a stroll up and down Main Street,” says Gagnon, whose enthusiasm for the many unique businesses in town is infectious. “But don’t forget the side streets,” she says. “It’s a beautiful walk, with lots of shops you’d hate to miss.”

Art + Antiques

To soak in some local culture, Gagnon suggests visiting the many art galleries and antiques shops. Among her favorites are the Wiscasset Bay Gallery and the Sylvan Gallery, both of which are owned and operated by artists. “You feel a deep appreciation for the visual delight in each,” says Gagnon. If you are an antiques enthusiast, Gagnon recommends visiting Michael Dunn Antiques and the Wiscasset Antiques Mall to go treasure hunting while you’re in town.

Be Sure to Sight-See

For the travelers coming to take in the historic buildings that the area is known for, Castle Tucker and the Wiscasset Old Jail are on Gagnon’s list of must-sees. Built in 1807, Castle Tucker is situated at the top of a hill overlooking the Sheepscot River and Wiscasset Village, where it housed three generations of the eponymous shipbuilding family. Today, it serves as a pristine example of Victorian architecture along the coast and is open for tours June through October. Opposite the opulence of Castle Tucker, the Wiscasset Old Jail—now run by the Lincoln County Historical Association—shows the sparse living situation of prisoners in the early nineteenth century.

Elevate Your Heart Rate

If you’re in the thrill-seeking mood, Gagnon says to check out the Wiscasset Speedway, less than three miles from downtown. Known as Maine’s biggest and fastest stock car racing track, the speedway hosts races every Saturday, April through October. If you prefer a quieter endeavor and have little ones to keep entertained, Gagnon recommends making your way over to Monkey C Monkey Do, an aerial adventure park with 60 different ropes courses, zip lines, laser tag, and a 35-foot swing that will make your heart race. Plus, Gagnon notes, “The safety training and a great, watchful staff make for a day of fun for all.”

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