15 Ways to Enjoy Your Stay!

July 22, 2021 / Art and Music, Food and Drink, Good to Know, History/Maritime, Outdoor Adventures, Things to Do & See

There are so many reasons to discover our beautiful historic and authentic coastal city. Here are 15 ways you, as a solo traveler or with your family and friends, can enjoy your stay any time of the year and simply fall in love with Gloucester, Massachusetts.

Stage Fort Park: Site of the landing of the first settlers in 1623, Gloucester became the second permanent settlement of the early Puritans in the New World, preceded by Plymouth in 1620. Enjoy the park with over 25 acres of natural beauty, including two beaches, a dog park, many walking trails and spectacular views of the harbor and beyond. There is a parking fee during peak summer season. Kids will love the playground baseball fields and tennis courts The Visitor Welcoming Center is open to visitors (May-October) to assist with brochures, maps and guides. Stage Fort Park is part of the Essex Coastal Scenic Byway.

Man at the Wheel Statue: The statue, also known as the Gloucester Fisherman Memorial, presides over Stacy Boulevard at the edge of Gloucester Harbor. Sculpted by artist Leonard Craske and modeled after a local fisherman, the monument was completed in 1925 in honor of Gloucester’s 300th anniversary. It has become the symbol of the city and a place to remember the 10,000 men lost at sea during the city’s long history. Their names are recorded on memorial plaques surrounding the structure.

Rocky Neck Art Colony/Cultural District: America’s oldest continually operating art colony (since 1850), Gloucester has played a vital role in America’s art history. Artists such as Fitz Henry Lane, Winslow Homer, John Sloan, Stuart Davis and Edward Hopper have all captured the light of Gloucester, as our many artists still do to this day. Gloucester’s Rocky Neck Cultural District is a compact, walkable area encompassing the peninsula of Rocky Neck situated within Gloucester’s working harbor.

Ravenswood Park: Explore a shrouded landscape of hemlock groves, a magnolia swamp, and other trees species where you’ll find remnants of Colonial habitation. Ravenswood Park offers 600 acres for solitude and quiet contemplation of nature. With 10 miles of carriage paths and trails that meander through the park, you can find plenty of room to picnic, bird watch, walk and simply appreciate the outdoors. You don’t want to miss trekking to the overlook to Gloucester Harbor or traversing the boardwalk through the Great Magnolia Swamp, home to native Sweetbay Magnolias.

Maritime Gloucester opens for its 21st season with so much to “Sea” and do. America’s oldest marine railway is your backdrop to experience the historic Gloucester working waterfront.  See how the Gloucester fishing fleet changed America and fed a nation. With historic buildings, interactive marine science exhibits, and the chance to sail aboard the Schooner Ardelle, maritime fun is around every corner.  Visit the Schooner Adventure, check out the Dory Shop, or check in the Mass Oyster Project.

Gloucester Schooners: For more than three centuries, the schooner has been the enduring icon of Cape Ann’s seagoing heritage. Fast and able, these sailing vessels capture the imagination of visitors and locals alike. No other type of vessel rivals its power and magnificence. It is impossible to climb aboard a schooner without feeling a deep connection to the thousands of daring fishermen who risked everything in search of fortune.  We invite you to spend a magical day on the Schooner Adventure or full moon cruise on the Thomas E. Lannon or a Sea Shanty gathering on the Schooner Ardelle.

Catch a Whale Watch in Gloucester, Cape Ann: One of the important eco-tourism industries in eastern Massachusetts is whale watching, with an estimated one million passengers heading out onto the ocean to view some of the largest animals on our planet. Most of those sea-going trips head out to Stellwagen Bank National Marine Sanctuary. Gloucester is considered the whale watch capital on the eastern seaboard because we are only 8 miles from Stellwagen Bank. Both 7 Seas Whale Watch and Cape Ann Whale Watch continue to take proper precautions to ensure your safety as you embark on a fun-filled tour. Give them a call and make your reservation today!

Harbor Tours: Enjoy a beautiful day out on the water with friends and family! Cape Ann Harbor Tours offers Daily Lighthouse Trips, Harbor Tours/ Lobstering Demonstrations, and Water Shuttle Hourly Trips. It’s such an enjoyable experience to see all that Gloucester Harbor and the Annisquam River have to offer. You’ll be glad you took the ride!

Fishing Charters: There is a myriad of Fishing and Charter boats to take you and your friends out for a fun day of excitement! Many offer Private Charters, Sightseeing, Lighthouse Tours, Photo Charters, Seal and Bird Watching, Ash Scattering, Private Scenic, Sunset, Harbor, and River Trips.

Sargent House: Built in 1782, the Sargent House was home to Judith Sargent Murray, one of America’s earliest advocates of women’s rights. Visit this beautifully preserved Georgian mansion to hear the life story of the remarkable 18th-century woman who published the groundbreaking essay “On the Equality of the Sexes” in 1790. See the “writing closet” where she produced works that were well ahead of her time. View period furnishings and works by Fitz Henry Lane, John Singer Sargent, and other notable artists.

Hammond Castle: The former home and laboratory of John Hays Hammond, Jr. Known as “The Father of Radio Control,” was one of America’s most prolific inventors and a protégé of Guglielmo Marconi, Nikola Tesla, Thomas Edison, and Alexander Graham Bell. Built from 1926 through 1929, and incorporated as a museum in 1930, the castle’s architectural style is mix of a medieval castle, medieval French village, and a Gothic cathedral. It was custom built to encompass Hammond’s private residence, laboratory, and museum-quality collection of architectural elements from his travels throughout Europe.

Cape Ann Museum and the new Cape Ann Museum Green celebrate the ongoing story of Cape Ann’s legacy of nationally significant historical, industrial, and artistic achievement through world-class exhibitions and engaging programs. Almost all of the collection has been gifted to the museum, mostly by family members of the artists. The collection of Fitz Henry Lane paintings from the 1800s, the Folly Cove textile designs exhibit, and the collections of furniture and sculptures from several centuries.

Shopping on Main Street: Gloucester’s charming Main Street features some of your favorite recognized brands, along with many unique, locally made items handcrafted by resident artists. Offering antiques, art, books, jewelry, toys, clothing, shoes, home goods and souvenirs – perfect for that one-of-a-kind gift to take home. Food lovers will also delight in the offerings on Main Street from unique olive oils, to fresh pasta, chocolate and cheese, to home Italian bread, not to mention many dining gems with outdoor seating options. There’s something for everyone on Main Street in Downtown Gloucester.

Outdoor Dining: Here are a few restaurants that are providing outdoor dining that coincides with the Massachusetts regulations as we continue to be cautiously optimistic with travel regulations.  For a more comprehensive list, visit our Dine page. Minglewood Harborside for large portions, several gluten-free choices, tons of open space for families, and attentive service. Mile Marker One is a beautiful setting right along the Annisquam River. Check out Blue Collar Lobster for downtown water views and great seafood. Amazing array of choices on the menu to bring to your outdoor table. 1606 Restaurant at the Beauport Hotel for outdoor seating on the waterfront and distinctive takes on traditional favorites. The stunning views are the perfect ambience for date night and special celebrations.