Fall Events on Cape Ann: Your Guide to Autumn Festivals and Seasonal Activities

August 22, 2025 / Uncategorized

Fall on Cape Ann is a season of color, creativity, and community. As the leaves turn and the air crisps, the region comes alive with events celebrating art, food, fashion, and the unique coastal culture that makes Gloucester, Rockport, and Essex so special. Whether you’re a longtime local or visiting for the first time, these fall events are not to be missed.

Blackburn Brew Fest

For craft beer lovers, the Blackburn Brew Fest is a highlight of the season. Sample brews from local and regional breweries while enjoying live music, food vendors, and the vibrant atmosphere of the harbor. It’s the perfect way to toast the changing seasons all while supporting Cape Ann Community Foundation.
Date: September 13
Location: Stage Fort Park

Thrift the Runway: The Open Door Fashion Show

Fashion meets philanthropy at Thrift the Runway, an annual show hosted by The Open Door. Local designers and community members showcase creative outfits made from thrifted finds. It’s a fun, sustainable twist on fashion and a great way to support a local cause.
Date: September 14
Location: The Cut

Cape Ann Plein Air

Art lovers won’t want to miss Cape Ann Plein Air, a multi-day event where artists paint outdoors, capturing the stunning landscapes, historic streets, and coastal charm of the region. Visitors can watch the creative process, attend artist talks, and purchase original works.
Date: October 4-12
Location: Multiple locations across Cape Ann

Cider and Donut Cruises with Essex River Cruises

Combine scenic fall foliage with delicious treats on Cider and Donut Cruises with Essex River Cruises. Sail along the Essex River while enjoying fresh apple cider and donuts—an ideal way to soak in the season from the water. Perfect for families and couples alike.
Date: Weekends in October
Location: Essex River Cruises

Cape Ann Artisans Fall Tour

The Cape Ann Artisans Fall Tour is your chance to visit local studios and meet artists in their creative spaces. From painting and ceramics to jewelry and woodworking, you’ll discover unique pieces perfect for gifts or personal treasures. This self-guided tour highlights the region’s thriving arts community.
Date: October 11-12
Location: Multiple locations around Cape Ann

Spiritualism Tours by Candlelight at Hammond Castle Museum

For a spooky and historical experience, try the Spiritualism Tours by Candlelight at Hammond Castle Museum. Learn about the castle’s fascinating history and the spiritualist movement while exploring its candlelit halls—ideal for a chilly October evening.
Date: Every Thursday night, now through October 
Location: Hammond Castle Museum

 

Essex Clam Fest

Seafood fans will love the Essex Clam Fest, a celebration of Cape Ann’s working waterfront and famous clam chowder. Enjoy food vendors, live music, and family-friendly activities while tasting some of the best local seafood.
Date: October 25
Location: Shepard Memorial Park in Essex, MA

Rockport Harvest Fest

Don’t miss Rockport Harvest Fest, a festival of local produce, crafts, and entertainment. Wander the streets of this charming seaside town while enjoying seasonal treats, artisan goods, and live performances celebrating the bounty of the fall harvest.
Date: October 18
Location: Multiple locations around Rockport, MA

Visit Cape Ann This Fall

Fall on Cape Ann offers something for everyone—from craft beer and fashion to art, seafood, and seasonal festivities. Whether you’re planning a weekend getaway or a day trip, these events provide the perfect opportunity to experience the region’s creativity, history, and community spirit. Mark your calendars, bundle up, and get ready to enjoy the best of Cape Ann this fall.

View the full events calendar here or click here to plan your fall trip to Gloucester, MA.