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We all know Halloween is coming. And we have plenty of ideas for how you can immerse in the thrills and chills of the season. But even without pumpkins and ghouls, October on the North Shore is a glorious time in its own right, so we’ve also assembled a list of things to do in the region that are spectacular without being spooky.

Cape Ann Plein Air

1. Cape Ann Plein Air, throughout Cape Ann | Oct. 1-9
Catch a glimpse of professional artists practicing plein air painting, a technique in which painters work outdoors and paint the landscapes they see before them. The nine-day celebration and competition includes a lineup of events art sales, demonstrations, gallery talks, and artists dinners. Check out the full schedule at

2. Cardboard Boat Regatta, Inner harbor, Manchester by the Sea | Oct. 9
It’s exactly what it sounds like: Teams build a boat out of cardboard, then compete to see who can paddle a simple route fastest, ideally without sinking. Join to crowd at 11 a.m. to root for your favorite, or get moving and build your own last-minute entry. Details at

Manchester by the Sea Cardboard Boat Regatta

3. Harvest Fest, Patton Homestead, Hamilton | Oct. 13-15
Celebrate the harvest season by supporting local music, local food, local craft brews, and local farms. Highlights include live music on Thursday night, an outdoor showing of Field of Dreams on Friday, and a whole afternoon of family fun on Saturday. Visit the Patton Homestead website for details.

4. Ipswich Illumination, downtown Ipswich | Oct. 14-16
For three days, Ipswich celebrates art and culture with live music, art, interactive installations, dance parties, poetry, and more. The centerpiece is Saturday evening, when an illuminated path connects viewing points along the Ipswich River, offering views of floating bonfires lighting up the water. More details are available at the Historic Ipswich website.

5. Costume Trunk Show, Peabody Essex Museum, Salem | Oct. 14-15
Shop a collection of unique headdresses, crowns, and fascinators created by Dora Marra, owner of Head Dress NY and the designer behind some of the fabulous pieces you’ve seen on the pages of Vogue and Cosmopolitan including the crow headband worn by Moira Rose on Schitt’s Creek. Details available on the museum website.

Dora Marra headpieces

6. Oktoberfest weekend, Appleton Farms, Ipswich | Oct. 15-16
German-inspired pizza, lawn games, local breweries, and an oompah band bring the fun of Oktoberfest to Appleton Farms. Pre-registration is encouraged.

7. LEGO train, Wenham Museum, Wenham | Oct. 15-16
Enthusiasts of all ages will be fascinated by this model railroad that circles through a meticulously created LEGO landscape of skyscrapers, cottages, ski slopes, and more, including some Halloween surprises. Advanced reservations are strongly encourage and can be made at the museum website.

8. Vintage car climb, Castle Hill on the Crane Estate, Ipswich | Oct. 16
Spend the day watching cars dating back before World War II racing up the winding roads of Castle Hill. Local food vendors and breweries will be selling their wares, and historically themed tours of the hilltop mansion will be available. For more details, visit the Trustees website.

9. Celebrating David Bowie, The Cabot, Beverly | Oct. 20
Rock & Roll Hall of Famer Todd Rundgren leads a group of acclaimed musicians in a live performance paying tribute to David Bowie. The performers promise songs for every Bowie fan and will endeavor to answer the question “What makes Bowie different?” Tickets and more details are available at

10. Essex ClamFest, Shepard Memorial Park, Essex | Oct. 22
The 38th annual Essex Clamfest will feature arts and crafts shows, live entertainment, and food vendors on site. But the highlight is the chowder tasting, in which local restaurants compete to see who cooks up the best version of the classic North Shore soup. Details available online.