Fall Dining Guide: Restaurants and Seasonal Flavors in Gloucester, MA

August 18, 2025 / Food and Drink, Good to Know

Fall in Gloucester, Massachusetts, is the perfect time to enjoy the coast with fewer crowds, cooler weather, and plenty of seasonal flavors. Whether you’re looking for a cozy dinner, casual bites by the water, or something fun to do before or after a meal, Gloucester offers a variety of options. Here’s a guide to where to eat in Gloucester this fall:

Cozy Dining at 1606 Restaurant & Oyster Bar

Located at the Beauport Hotel, 1606 Restaurant & Oyster Bar is a great choice for a cozy dinner with harbor views. The restaurant highlights fresh seafood and classic New England fare with a modern touch. In fall, it’s a welcoming spot to enjoy local oysters, hearty entrees, and seasonal sides while watching the sunset over Gloucester Harbor.

Chowder at Gloucester House

No trip to Gloucester is complete without a bowl of clam chowder, and Gloucester House has long been a staple for this classic dish. Their creamy chowder is rich with clams and flavor, making it a must-try for visitors. The restaurant also overlooks the working waterfront, offering a true taste of Gloucester both on the plate and in the view.

Sushi and Smash Burgers at Minglewood Harborside

If you’re traveling with a group or just want variety, Minglewood Harborside delivers. The menu features everything from fresh sushi rolls to smash burgers with crispy edges and plenty of toppings. It’s a casual, harborside spot where you can mix and match lighter bites with comfort food, making it a solid option for a fall evening out.

Dinner and Activities: Harbor 9 Golf & Cape Ann Lanes

Gloucester also offers options to combine dining with something fun to do all year long. At Harbor 9 Golf, you can play a round on indoor golf simulators, making it a fun choice for fall when the weather cools. Pair your game with dinner and drinks, or just hang by the bar for a full night out.

For family-friendly fun, Cape Ann Lanes offers candlepin bowling, an arcade, and its own brewery. Visitors can enjoy a casual meal and drinks while bowling, making it a great all-ages evening activity.

Seasonal Treats at Turtle Alley Chocolates

Fall also means seasonal sweets, and Turtle Alley Chocolates is the place to go. Known for handmade chocolates and creative candies, they often feature fall-inspired treats like candy apples. It’s a fun stop to pick up a snack or bring home something special.

Fall Flavors at Holy Cow Ice Cream Café

Ice cream isn’t just for summer. Holy Cow Ice Cream Café is known for its inventive flavors, and in fall they often highlight seasonal combinations with maple, apple, or warming spices. Whether you enjoy it on-site or take a pint to go, it’s a favorite stop for visitors year-round.

Dining by the Water at Mile Marker One

Located at The Hotel at Cape Ann Marina, Mile Marker One offers indoor and outdoor seating along the Annisquam River. The menu balances local seafood with creative seasonal dishes, and the riverside setting makes it a relaxing spot to enjoy a fall meal. From fresh catches to comfort food favorites, Mile Marker One is a favorite spot for both visitors and locals.

Wood-Fired Cooking at Oak to Ember

For something a little heartier, Oak to Ember specializes in wood-fired cooking with a focus on steak and seafood. The open-flame preparation adds depth and warmth to every dish, creating a dining experience that feels especially fitting in cooler months. Located downtown, it’s an easy choice for a fall night out in Gloucester.

Plan Your Fall Adventure in Gloucester, MA

Beyond great dining, Gloucester has plenty of ways to enjoy fall on Cape Ann. From scenic coastal walks to seasonal events and local shopping, it’s the perfect time to explore everything the area has to offer. Be sure to check out our guide to planning your fall trip for even more ideas.

Featured image credit: Marnely Murray