Why not explore Main Street, Gloucester?  

You might be surprised to discover all the offerings in our downtown! Going all the way back to the beginning, our historic and picturesque Courthouse dates back to the late 1600s. You’ll be able to see history up close when you visit the original Courthouse, the Clayton and Roane Buildings, as well as the old debtors’ prison.

Learn about the history of our town in the Gloucester Museum of History exhibits at the Botetourt Building, just off the Courthouse Circle. For fun, imagine yourself as a Courthouse judge or prisoner!  Gifts are available at the Visitors Center, if you would like a souvenir from your visit. 

Wander down our beautiful Main Street and you’ll soon discover a variety of boutique shops and restaurants. For hearty American fare, dine at Olivia’s, or head to Sweet Tooth for great salads, sandwiches, and desserts. Try Bangkok Noi for delicious Thai food, or Porter’s on Main for fine dining. For a fun and casual outing, stop by the Gloucester Brewing Company for a beer. Want something to take home? Stop to buy fresh fish and produce at Ware Neck Produce, or peruse the extensive wine selection and specialty meals at Kelsick Specialty Market.  Whatever your taste, you’ll find something to enjoy!

As you walk, experience the gorgeous public artwork commemorating the cultural, social, and economic history of our community: murals of Pocahontas, TC Walker, as well as the Watermen, Bees on Main, and of course, Daffodils; plus the sculptures which highlight our town and the surrounding environment. Enjoy the planted hanging baskets and daffodil banners which line our streets. Take time to chat to the shopkeepers, and ask them why they choose to be on our Main Street—you’ll be amazed how strong the support is for our local business owners!