Gloucester Like a Local: Exciting Things to Do in Fall on Cape Ann

Autumn in New England is pure magic, and there's no better place to experience it than on Cape Ann. Bring your autumn adventures to Gloucester, where the salty air and crisp fall colors create a perfect backdrop for adventure. From hidden gems and historic spots to delicious bites, discover why locals love this time of year and find your next favorite fall activity on the coast. 

Taste Gloucester: A Guided Local

For a unique and delicious fall activity, sign up for a Taste Gloucester walking tour. This is more than just a food tour; it's a journey where you'll explore the city's rich history while enjoying the best of its culinary scene. Your tour begins at the Beauport Hotel, where you can warm up with a bowl of our award-winning clam chowder before heading out. You’ll learn about the area's heritage—from its beginnings as America's oldest seaport to the innovative Birdseye "flash freeze" plant that once stood where the hotel is today. It's the perfect way to spend an afternoon and eat well, too. Call our Concierge Desk for tickets and information at 978-282-0008 Ext. 5.

Cape Ann Whale Watches

The ocean comes alive in the fall, and there's no better way to experience it than on a whale watching tour. With Cape Ann Whale Watch, you're in for an unforgettable experience. The crisp autumn air on the open water makes for a truly invigorating adventure. Embark on an unforgettable whale watching experience with Cape Ann Whale Watch, where guaranteed whale sightings await! Their fall schedule (October 1 – November 2) is Saturday and Sunday 8:30AM and 1:30PM; Monday – Friday 10AM only.

Beauport Cruiselines: Harvest Cruises

Beauport Cruiselines offers a stunning way to experience Gloucester Harbor in true New England style. As the vibrant hues of autumn emerge, our Fall Harvest Cruises provide a beautiful perspective on the season. Once aboard, you'll sail past historic landmarks, charming fishing boats, and the Cape Ann coastline, all set against a backdrop of crisp fall air and the changing foliage of America's oldest seaport. It's the perfect opportunity to indulge in an exquisite meal, enjoy live entertainment, and toast to the beauty of a Gloucester autumn.

Autumn on Cape Ann Guide

This is just a glimpse of the vibrant, history-rich, and beautiful autumn that awaits you in Gloucester. There's so much more to see, taste, and explore as the seasons change. From finding the perfect hiking trail to capturing that ideal foliage photo, you can find more autumn activites and book your next adventure, our complete Autumn on Cape Ann Guide. We look forward to welcoming you to the coast!