5 Things to Do in Gloucester

Gloucester’s walkable Main Street welcomes exploration of fine dining, grabbing a quick bite, or savoring a specialty coffee to start the day’s adventure — Main Street has your favorite flavor. Along the way, art is tucked into every corner, unique specialty shops offer treasures to browse, and history comes alive on the very streets. It’s a charming destination with the feel of a Hallmark movie.

Visitors Center

History from Native Americans, to colonial, Revolution, and civil rights eras, Gloucester has stories to tell. Located next to the Colonial Courthouse, the Visitors Center (open Tuesdays through Saturdays 10 a.m.-4 p.m. and Sundays and Mondays 1-4 p.m.) is the perfect starting point for your Main Street adventure. Here, guests can get personalized recommendations for the best shopping and dining, browse local artisan crafts in the gift shop, and explore the fascinating Werowocomoco Exhibit — a preview of the future National State Park, planned for the shores of York River of Gloucester. Werowocomoco was the capital of the Powhatan Chiefdom where he lived with his daughter, Pocahontas.

Tour

Tourism ambassadors are awaiting right next door in the historic Courthouse Circle for a personalized tour on Saturdays 10 a.m.-4 p.m. and Sundays 1-4 p.m. On Oct. 26 at 3 p.m., the Gloucester Museum of History will celebrate the grand opening of its new expansive second floor exhibition, featuring the daffodil industry, watermen, military, and the first 400 years of the county.

Art

Quaint Gloucester Main Street is filled with charm, from eye-catching statues to vibrant historical murals. Start your day with a coffee or boba tea in hand and stroll while soaking in the art. Stop by Arts on Main (Wednesday through Saturday noon-5 p.m.) or the Gloucester Fine Arts Museum (Tuesday through Saturday 10 a.m.-5 p.m.). Together, they make Main Street the perfect destination for art lovers and explorers alike.

Park

Gloucester Main Street is also pet-friendly, making it easy to bring four-legged friends along for the adventure. Take a break at Tucker Park, just outside the historic Colonial Courthouse circle, where you can relax and enjoy the charm of the town. With multiple lunch spots offering outdoor seating, it’s the perfect place to savor a meal with your furry best friend.

Daffodil Festival

If Gloucester charms you in the fall, plan to return in the spring for the 40th Annual Gloucester Daffodil Festival, on March 28 and 29, 2026. This beloved tradition celebrates the season with golden blooms, delicious food, live music, fine crafts, living history, and so much more, and welcome spring — Gloucester style!