Fall in Gloucester brings crisp sea air, stunning foliage, and seasonal charm at every turn. Explore downtown shops, enjoy a cozy meal with a harbor view, or stroll scenic trails framed by autumn color. From apple cider and seafood chowder to art walks and local happenings, there’s no better place to soak in the season than Gloucester. Come experience the magic of autumn by the sea.
Things To Do
Cape Ann Whale Watch
The pioneers of whale watching in Gloucester since 1979, entering our 47th season! Sail aboard the Hurricane II, the largest & fastest vessel out of Gloucester. FREE PARKING & voted 5 stars on Trip Advisor!
Hammond Castle Museum
A dynamic STEAM museum, blending its historical significance as both a historic house museum and a lapidarium. Listed on the National Register of Historic Places, Hammond Castle Museum was recently recognized as a Northshore Magazine Best of North Shore Reader’s Choice winner in three categories, including Museum, and a TripAdvisor Traveler’s Choice award recipient for the last four consecutive years.
Fall in Glouester, MA: Things to Do in America’s Oldest Seaport
From art walks to harbor tours, cozy restaurants to coastal hikes, and so much more, here’s how to spend a fall day (or weekend) in America’s oldest seaport.
Places To Stay
Cape Ann Motor Inn
Located directly on the sands of Long Beach in Gloucester, MA, Cape Ann Motor Inn is open year-round, with all rooms and kitchenettes overlooking the ocean with views of the twin lighthouses of Thacher Island. You will be amazed at the unforgettable sunrises.
Harborview Inn
Located on Stacey Boulevard and diagonally across from the iconic Man at the Wheel statue, the Harborview Inn is within walking distance of downtown’s restaurants, museums, shops, and attractions.
The Hotel at Cape Ann Marina
The Hotel at Cape Ann Marina is open year-round featuring on the water rooms with balconies overlooking beautiful saltwater marshes and marina on the beautiful Annisquam River. Located close to downtown, historic sites, Stage Fort Park and recreational destinations.
Ocean House Hotel at Bass Rocks
Picture-perfect views of the Atlantic Ocean and rocky shoreline inspire you to unwind in comfortable rooms and suites with private patios and verandas. Enjoy complimentary seaside breakfast each morning and watch the sun set by the fire pit every evening. Relax, unwind and play at this historic New England retreat at the edge of the ocean.
Sea Lion Motel & Cottages
The Sea Lion Motel offers a variety of lodging options near beaches, restaurants, shops and attractions. Motel rooms offer a choice of queen, king or two double beds. The Main House offers two house suites and a deluxe king room. Three Cottages are located in the upper portion of the property, all recently renovated with fully equipped kitchens and private decks.
The Vista Motel
With its gorgeous views overlooking Good Harbor Beach and comfortable rooms, The Vista can be your home away from home during your next getaway to Gloucester, MA. Each room is spacious, clean, and has a breathtaking view of the ocean from your room’s patio or private balcony. A light Continental Breakfast can be enjoyed on our tented breakfast pavilion.
Dining
Mile Marker One
You can dine at the water’s edge on the freshest seafood from our boats to your plates – year-round here. Something for everyone: fresh inspired lobster dishes, chowders, salads, pastas, grass-fed beef, and sautés, with excellent flavor for really “great” food.
Fall Dining Guide: Restaurants and Seasonal Flavors in Gloucester, MA
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.
Shopping
Second Glance Thrift Store
You never know what you’ll find when you shop at Second Glance Thrift Store, the thrift store of The Open Door. Come in and browse through their ever-changing inventory from clothing to jewelry, from housewares to furniture, from books and games to music. Proceeds support local hunger-relief programs available through The Open Door.
Turtle Alley Chocolates
Come to Turtle Alley for the freshest caramel, fudge, toffee, and chocolates around! Handmade with all the love. Our caramel apples are LEGENDARY. Life is short. Sin a little!
Your Guide to Fall Shopping in Gloucester, MA
Gloucester is the perfect destination for a fall getaway — and there’s no better time to refresh your wardrobe, update your home, and stock up on seasonal flavors from local shops.
Fall Events
Cider & Donut Cruises with Essex River Cruises
October 4, 2025
Join Essex River Cruises this all and cruise up close…
Cider & Donut Cruises with Essex River Cruises
October 5, 2025
Join Essex River Cruises this all and cruise up close…
Cape Ann Artisans Fall Tour
October 11, 2025
Join 14 Cape Ann Artisans for a creative journey through…
Cider & Donut Cruises with Essex River Cruises
October 11, 2025
Join Essex River Cruises this all and cruise up close…
Cape Ann Artisans Fall Tour
October 12, 2025
Join 14 Cape Ann Artisans for a creative journey through…
Cider & Donut Cruises with Essex River Cruises
October 12, 2025
Join Essex River Cruises this all and cruise up close…
Rockport Harvest Fest
October 18, 2025
The Greater Cape Ann Chamber of Commerce presents Rockport’s Harvest…
Cider & Donut Cruises with Essex River Cruises
October 18, 2025
Join Essex River Cruises this all and cruise up close…
Cider & Donut Cruises with Essex River Cruises
October 19, 2025
Join Essex River Cruises this all and cruise up close…
The Madness within the Abbadia Mare: Inspired by the Tales of Edgar Allan Poe
October 20, 2025
1920s Halloween gathering, and journey through time and space as…
Cider & Donut Cruises with Essex River Cruises
October 25, 2025
Join Essex River Cruises this all and cruise up close…
Cider & Donut Cruises with Essex River Cruises
October 26, 2025
Join Essex River Cruises this all and cruise up close…
Silent Movie: Phantom of the Opera with Live Accompaniment by Peter Krasinski
October 26, 2025
Internationally acclaimed, silent film live accompanist, Peter Krasinski, returns the…
Metropolis with Live Accompaniment by Peter Krasinski
October 27, 2025
Internationally acclaimed, silent film live accompanist, Peter Krasinski, returns to accompany…
Costumes & Candlelight: Self-Guided Tours After Dark
October 28, 2025
Avoid the crush of crowds and enjoy Halloween week with…
Costumes & Candlelight: Self-Guided Tours After Dark
October 29, 2025
Avoid the crush of crowds and enjoy Halloween week with…
Renaissance Faire Day at Hammond Castle Museum
November 8, 2025
Rain or Shine! Step back in time at our Renaissance…
More to Explore:
Getting Around Gloucester Just Got Easier: Ride CATA for Free Through the End of the Year
Whether you’re planning a beach day, heading to a local festival, or just exploring downtown Gloucester, there’s never been a better time to hop on public transportation. The Cape Ann Transportation Authority (CATA) is offering free rides on all fixed-route buses and ADA/DAR van services through the end of the year—making it even easier and more affordable for visitors to enjoy everything the area has to offer.
Discover One-of-a-Kind Treasures at Second Glance
Just a short drive from Good Harbor Beach, and on the way to Rockport, is a hidden gem loved by locals, snowbirds, and tourists alike on Cape Ann: Second Glance, thrift store of The Open Door.
Plan Your Visit
Plan your perfect fall getaway and find things to do in Gloucester with our guide to the best places to shop, stay, dine, and explore this season!
Shop
Shop for unique gifts and souvenirs at Gloucester’s local stores, where you’ll find handcrafted treasures and coastal-inspired items, perfect for the season.
Stay
Stay in one of Gloucester’s charming inns, hotels, or B&Bs, offering cozy accommodations by the sea or in the heart of downtown.
Dine
Dine at Gloucester’s local restaurants, serving fresh seafood and seasonal dishes to warm you up after a day of exploring.
Things to Do
From festive events to year-round attractions, there’s plenty to experience during your visit to Gloucester.
Funded, in part, by the Massachusetts Office of Travel and Tourism.
