Discover Gloucester

10/22/2026

From the Deep returns to Downtown Gloucester on Saturday, November 7! 🎨

Celebrate Gloucester’s vibrant arts and culture scene with a day of free art exhibitions, live performances, artist demonstrations, and hands-on activities throughout downtown from 11 AM–5 PM.

10/21/2026

Your fall itinerary needs a castle! 🏰🍂

Perched along Gloucester’s rocky coastline, Hammond Castle Museum is one of the North Shore’s most unique attractions. Built in the 1920s by inventor John Hays Hammond Jr., this medieval-style castle is filled with fascinating history, art, and architecture.

And there is still time to experience this fall's special events at the museum, including:

🕯️ Spiritualism Tours by Candlelight on Thursday nights: Explore the Hammonds’ fascination with the supernatural on a guided evening tour.

🎃 Costumes & Candlelight on October 27: Dress up and explore the castle's halls and galleries by candlelight.

⚔️ Renaissance Faire on November 7 & 8: Step back in time with armored combat demonstrations, live entertainment, artisans, and more!

10/16/2026

A little coastal scenery from Rafe's Chasm. 🌊

One of our favorite spots to take in Gloucester's beautiful trails and coastline!

10/13/2026

Heading to Destination Salem, Massachusetts this October? Add a whale watch in Gloucester to your North Shore itinerary! 🐋🌊🎃

7 Seas Whale Watch runs through October, and fall is a great time to head out on a trip to Stellwagen Bank to see Humpback Whales, Finback Whales, Minke Whales, and so much more.

Photos courtesy of 7 Seas Whale Watch

10/09/2026

Gloucester is getting some well-deserved love! 🌊♥️

Thank you Alexandra Nicole Nolan for featuring our historic seaport as one of Massachusetts’ most underrated weekend getaways:

Gloucester, Massachusetts, offers the perfect New England weekend escape with whale watching, historic attractions, waterfront dining, and plenty of coastal charm.

10/08/2026

Step inside the studios of Cape Ann’s talented artists this weekend! 🎨

The 43rd Annual Cape Ann Artisans Open Studios returns Saturday & Sunday, October 10–11, from 10 AM–5 PM. Explore studios throughout Gloucester and Rockport, meet the artists, watch demonstrations, and get a behind-the-scenes look at their creative process.

Plan your weekend and download the tour map at capeannartisans.com.

10/06/2026

Happy National Taco Day! 🌮

Celebrate in Gloucester with Machaca Tacos & Tequila, serving up traditional Mexican street tacos made with fresh ingredients, plus the largest tequila selection on the North Shore.

10/05/2026

The dahlias are showing off on Stacy Boulevard!🌸

Take a stroll along the boulevard to see these colorful blooms, lovingly planted and cared for by GenerousGardeners.

10/03/2026

Cape Ann Plein Air kicks off today! 🎨🍂

Over the next week, watch talented artists capture the coastal landscapes, historic streets, and waterfront views of Gloucester and Cape Ann, all painted outdoors and on location.

Events run through October 11, with opportunities to see the artists at work, experience freshly painted works, and celebrate Cape Ann’s incredible arts community.

Explore the full schedule at capeannpleinair.org!

Photos 1 & 3 by Neal Levy
Photo 2 by Cape Ann Plein Air Staff

10/02/2026

There’s so much happening on Cape Ann this fall! 🍂🎨

From art events and open studios to Halloween celebrations, seasonal tours, workshops, and more, add these upcoming events to your calendar:

Discover upcoming events on Cape Ann this fall, from Halloween parties and ghost tours, to artist workshops, and so much more.