Welcome to Gloucester – you’ve arrived at the perfect place for breathing. We all know that fresh air is a key to health, happiness and sparking an appetite. You’ll need that appetite during your stay—with new restaurants to experience, new art galleries to inspire and new adventures to embark on. On the eve of celebrating its 400th birthday in 2023, Gloucester is one of the U.S.’s most popular coastal destinations—and home to America’s oldest working seaport—promising stunning beaches and sunsets. It’s also an ever-evolving community, and you’ll notice new shops, cultural venues and neighborhoods.

As Gloucester moves forward, it honors its past. Fishermen still head out to sea each morning and battle the unpredictable waters (The Fishermen’s Memorial will tell you more). Artists remain inspired by Cape Ann’s elusive light and strive to capture it on canvas, from dawn to dusk. Beaches and natural resources remain protected and pristine. Gloucester takes great pride in its traditions yet welcomes visitors and new residents to join in every aspect of its culture.

While downtown you’ll notice a bustling Main Street boasting locally owned retail shops, galleries, cafes and fine restaurants. Rogers Street, running parallel to Main, adds its own restaurants and shops, along with access to whale watching, schooner sails, and other waterfront recreation. While meandering downtown, visit the Cape Ann Museum and learn more of the city’s history, its settlement in the early 1600s and its journey to becoming one of the world’s largest fishing ports by the mid 1800s. You’ll also stand in awe at the paintings of Fitz Henry Lane, Winslow Homer and others.

History, arts and culture, the freshest sea-food—and some of the best ice cream and pizza to be found—Gloucester has thought of everything. And after a great dinner, live music awaits at any number of venues.

If you’re here to relax, Good Harbor and Wingaersheek beaches, to name just two, will transport you to a calmer place. The salt air, combined with a long walk or kayaking, will restore and invigorate.

Perhaps one of Gloucester’s best-kept secrets is its off-season. Special rates entice and cooler temps are often more invigorating. Winter hiking, cross-country skiing, ice skating and bird watching will fill your days. There’s also a fascinating concentration of winter seabirds—take the Cape Ann Winter Birding Boat Trip to Stellwagen Bank. In fact, “off” season is the new “on.”

Community Highlights