Fall For Gloucester

Experience Gloucester’s autumnal beauty this fall season. From waterfront dining and whale watches, to scenic hiking and boating, trails, sails, tours, and fresh local seafood, Gloucester offers the best of autumn in New England, by land and sea!

The fall season has arrived in Gloucester! The smells of cinnamon and fresh baked bread waft from storefront windows on Main Street, dahlias are dazzling Stacy Boulevard along the ocean, and bright colored foliage is starting to peak out around our rocky coastline. Some argue that autumn is the best season to visit “the island you can drive to.” Enjoy Gloucester’s world-class fresh seafood, ample boating offerings, and crowd-free beaches, and try something new while you’re here. 

Explore Gloucester’s Great Outdoors

    • Dogtown Common in Gloucester spans across 3600 acres of undeveloped woods, including a vast series of trails. Read “Step Into the Past in Dogtown” by Gloucester Writers Center to learn about its Indigenous and settlement history, and where you can find a map for exploration of the wooded trails. Dogtown has inspired writers and artists for generations, like published poet Diana Rose Lynch. Click here to read her works “Passing Through” and “Requiem for Sarah Jacobs Philips” provoked by her research of Dogtown.
      • Gloucester has ample running route options. Whether you’re an everyday runner, a weekend trail runner, or a now-and-then downtown jogger, you can find your perfect running trail, pace, and scenery in Gloucester. Explore Dogtown woods through the eyes of a local runner and nature lover in Heather Atwood’s piece “Spending Time in Deer World.” 
          • If you’re exploring Gloucester with your canine companion in tow, the beaches “go to the dogs” starting October 1! Read “Dog Days of Autumn” by Heidi Wakeman for tips on which beaches require leashes and which don’t and on which days of the month. Heidi’s poem “Good Harbor Beach Goes to the DOGS!” will inspire you to soak up the fall fun with your pup on the sand.
            • Cyclists, find your zen with an Inspiring Ride along the winding, rolling roads of Gloucester and Rockport. With scenes like these, you’ll start to understand why locals never want to leave the island. Click here for a guide to the scenic seaside bike ride of your dreams
                • Gloucester is a prime destination for swimmers, as well. After a hot summer of sun, the water is still warm throughout the fall season. Some stick to warm water dips, while others practice cold water swimming all year round. Local writer, poet, and swimmer Bob Goodman writes about Cape Ann’s dramatic tides and his daily swims on the Annisquam River from April through mid October in his piece “Biding the Tides in Gloucester,” which includes his inspired poem “What is real.”

                  Autumn Arts & Entertainment in Gloucester

                      • Gloucester’s arts and culture roots run deep. Explore the many galleries in downtown Gloucester and on Rocky Neck. Rocky Neck Art Colony has been a long-time home to local artists and their galleries, as well as local writers and poets. Click here to read poetry about Gloucester in the fall from local poet, yogi, and certified dreamwork professional Jennie Meyer.


                      Downtown Shopping & Local Comfort Food

                        • Lovers of pumpkins, pumpkin flavored foods, and pumpkin cocktails, read Kathleen Williams’ piece The Great Gloucester Pumpkin Expedition for a quirky, curated list of delicious local treats on Main Street in Gloucester and around Cape Ann. Seeking more inspiration for exploring downtown Gloucester in the fall? Cozy up and read Adam Tessier’s Poet’s Day Off: A Writer’s Eye on Downtown Gloucester and plan your day of coffee sipping, thrifting, record collecting, museum visits, and more in Gloucester this autumn. All that’s missing are your flannel and boots!


                      Boating & Maritime History


                      Stay, play, dine and explore Gloucester, MA this fall season.

Funded, in part, by the Massachusetts Office of Travel & Tourism