This Small Massachusetts Town Has The Best Downtown

Some towns have a single claim to fame: art, food, or outdoor adventures. Rockport, Massachusetts? It refuses to choose. This coastal town has it all. And impressively, most of the fun happens right downtown, so you can park the car and walk from site to site throughout the weekend. Strolling through the streets, you can explore iconic art landmarks, museums, performing arts venues, beaches, breweries, and lobster houses all within a few blocks, giving you a full-on New England experience in one go.

Motif No. 1

Ask any Rockport resident what the town’s most distinguishable landmark is, and nine times out of 10, they will name Motif No. 1. Located right downtown, on Bradley Wharf, this iconic red shack is historically one of the most painted buildings in the United States. Its fame goes back to the mid-19th century, when Rockport grew as both an art colony and a fishing village. Painters repeatedly attempted to capture it on canvas, and over time, it became a defining symbol of New England life. Although the original building was unfortunately lost in the Blizzard of 1978, the replica that stands in its place continues to honor the original icon.

Does this legendary fishing shack pique your interest? Consider scheduling your visit to Rockport in May, during the annual Motif No. 1 Day. This family-friendly event celebrates the beloved building with activities such as a Motif No. 1 plein air paint-out, a walking tour, live music, food trucks, games, and more.

Museums, Galleries, & Performing Arts Venues

As one of the country’s oldest art colonies, Rockport offers far more than Motif No. 1 when it comes to its vibrant art scene. There are over 30 galleries to explore in town, along with the famed Rockport Art Association and Museum. This museum preserves and showcases artwork from Cape Ann, some of which dates back over a century. It also hosts numerous rotating exhibits throughout the year, along with workshops, classes, and other educational programs. If you are hoping to add a new piece to your collection, consider visiting nearby galleries like the Lauri Kaihlanen Gallery, known for its whimsical wildlife paintings, or the Art Nook Gallery, which showcases work from three local artists.

Care for some live entertainment? The Rockport Music-Shalin Liu Performance Center, situated right on Main Street, is the perfect place to attend a show. The arts organization, Rockport Music, has been bringing performances to the community for more than four decades and opened the current Shalin Liu Performance Center in 2010. You’ll be able to enjoy all kinds of shows here, including jazz concerts, film screenings, holiday performances, and much more.

Beaches & Water Recreation

After you spend some time exploring Rockport’s art scene, you’ll likely want to spend some time exploring the beaches or water if the weather is nice. You’ll find several beaches within walking distance of downtown, one of the most popular being Front Beach. This beach sits on Sandy Bay and has lifeguards on duty during the high season. If you want to spend an afternoon paddling, consider arranging an excursion with North Shore Adventures and Outdoor Center. This local outfitter sits right on Tuna Wharf and offers several kayaking experiences, with seal- and bird-watching tours and island routes among the most popular. If you prefer stand-up paddleboarding, the agency can also occasionally arrange SUP tours upon request.

Coffee Shops, Restaurants, & Breweries

Topping off the downtown district is Rockport’s culinary scene. From breakfast through dinner, you’ll find all sorts of places to grab a bite or drink. If you happen to be in Rockport in the morning, you can start the day at Brothers Brew on Main Street. In addition to a cozy cup of coffee, this coffee shop serves some seriously delicious breakfast dishes, including breakfast skillets and burritos.

Roy Moore Lobster Company is another favorite, a lobster joint that has been serving the town since 1918. This spot is only open seasonally, but if you happen to be in town when it is, it is well worth the visit. Owned and operated by a father-son duo, this establishment serves fresh-cooked lobster, lobster rolls, and a raw bar, with all of the lobster being sourced from local inshore fishermen. If you are craving a cold beer, stop into Rockport Brewing Company, which is open Wednesday through Sunday. This brewery’s flagship beers include a New England IPA, an American Light Lager, a White Ale, an Italian Pilsner, and more.

A Downtown Packed With Entertainment

While many towns in Massachusetts have plenty to do, few pack it all into a downtown as compact and lively as Rockport. Here, you can enjoy a walk on the beach, an afternoon in a kayak, attend a live show, or grab a craft beer, all without ever needing to pull your car out of the lot. And this list is just the start: you are bound to uncover your own favorite spots while exploring town!