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Published on August 20, 2026

What’s Happening Cape Cod - October 2026What’s Happening Cape Cod

There’s no shortage of ways to enjoy October on Cape Cod, from fall festivals and community celebrations to road races, family-friendly activities and meaningful events supported by Cape Cod Healthcare.

Pink Pumpkins for the WED Fund

Pink PumpkinsThroughout October
Sandwich Glass Museum, 129 Main Street, Sandwich

In recognition of Breast Cancer Awareness Month, the Sandwich Glass Museum is offering hand-blown pink glass pumpkins to benefit the Cape Cod Women’s Cancer Prevention and Early Detection Fund (WED Fund) at Cape Cod Healthcare. Available in three sizes and a variety of pink hues, the individually handcrafted pumpkins range from $50 to $200 and can be purchased at the museum gift shop or online. A portion of October sales will support the WED Fund, which helps Cape Cod patients in need of financial assistance for breast diagnostic testing.

The museum will also host its annual Pumpkin Festival Oct. 11-12 from 10 a.m.-2 p.m., featuring its colorful collection of handcrafted glass pumpkins.

Cancer Survivors Day

Saturday, Oct. 3
11:30 a.m. – 1:30 p.m.
Margaritaville Resort Cape Cod, 1225 Iyannough Road, Hyannis

Staff from the Davenport-Mugar Cancer Center at Cape Cod Hospital and Clark Cancer Center at Falmouth Hospital invite cancer survivors and a guest to attend the 12th annual Cancer Survivors Day celebration.

This special afternoon will feature food, music, raffles, a photo booth, therapy dogs, inspiring words from cancer survivors and more. The event is an opportunity to celebrate those who have survived, inspire those recently diagnosed or undergoing treatment, and bring together families and friends in a supportive setting.

The event is free of charge, and advance registration is requested.

Orleans Community Resource Fair

Saturday, Oct. 3
11 a.m. – 2 p.m.
Nauset Regional Middle School

Stop by the Orleans Community Resource Fair and connect with local organizations and resources serving the Lower Cape community. Cape Cod Healthcare is proud to be a sponsor of this free community event.

The fair brings together local health, human services and housing organizations, along with Orleans town departments. Attendees can access free health screenings, vaccine information, tick education and car seat safety checks, as well as resources for housing, mental health, recovery support, veterans’ services, energy assistance and more.

The day will also feature an Orleans Fire-Rescue touch-a-truck, live music from Monica Rizzio and food available to purchase from Polka Dot Panini.

SandwichFest

Saturday, Oct. 3
10 a.m. – 3 p.m.
Water Street, Sandwich

Celebrate fall in the heart of historic Sandwich Village at SandwichFest along Water Street. This family-friendly community festival features a juried artisan craft fair, food trucks and local vendors, live PorchFest music, kids’ activities, a dog parade, antique cars, a beer and wine tent, and the popular sandwich-making competition. Admission is free. Cape Cod Healthcare is proud to be a Gold Sponsor of this community event.

Witches on the Water

Saturday, Oct. 3
3 p.m. – 5 p.m.
Oyster Pond Beach, 80 Stage Harbor Road, Chatham 

Watch a wave of fun-loving costumed witches take to their paddleboards at Oyster Pond Beach for Witches on the Water in support of Family Table Collaborative. The festive annual fundraiser includes food trucks, live music, raffles, prizes, a costume contest and photo ops. Free for spectators; paddlers $50 plus a $250 fundraising minimum. Registration opens at 2 p.m. Oyster Pond Beach, witchesonthewater.org 

Cape Cod Marathon Weekend

Saturday and Sunday, Oct. 10 & 11 
Races start at 8 a.m.
Mullen Hall School, 130 Katharine Lee Bates Road, Falmouth

Cape Cod Marathon Weekend is produced by the Falmouth Running Club and presented by Shipwrecked. Race weekend includes a marathon, a marathon relay, a half marathon, as well as a 5k! The Clam Chowdah Challenge is for those who would like to tackle both the marathon and the half marathon in the same weekend for a total of 39.3 miles. The new Lobstah Challenge is a fun event for those that want to run the half marathon and the 5k in the same weekend! Set against peak fall foliage, these scenic courses wind along Vineyard Sound and Cape Cod’s beautiful coastal roads. 

Yarmouth Seaside Festival

Saturday, Sunday and Monday, Oct. 10-12
10 a.m.-5 p.m. 
South Yarmouth 

The three-day festival is known for its family-friendly atmosphere and community spirit, with activities including live music, an arts and crafts fair, food vendors, pie-eating contests, sand sculpture contests, a 5k road race, canoe and kayak races, carnival attractions, a beach bonfire and fireworks. 

Joshua Sears Memorial Field, 1175 Route 28 and Wood Road, South Yarmouth 

Chatham Bars Inn Farm Fall Frolic

Sunday, Oct. 11
11 a.m.-5 p.m.
Chatham Bars Inn Farm, 3037 Main St., Brewster

Celebrate the season with live music, lawn games, pumpkin painting and fresh cider donuts at this family-friendly event. Two sessions: 11 a.m.–2 p.m. or 2–5 p.m. Tickets $10 for ages 12+, children free. Sign up on Eventbrite. Proceeds support Brewster Sea Camps and local youth sports. Parking at former Brewster Sea Camps across from the farm. Tickets are $10. Rain date: Monday, Oct. 12.

Wellfleet OysterFest

Saturday and Sunday, October 17 & 18
10 a.m.-5 p.m. 
Downtown Wellfleet

This two-day family festival celebrates the town’s famous oysters, clams and shellfishing traditions — and brings together locals and visitors alike for a weekend full of hometown flavor and big-time fun! There is something for everyone at OysterFest: Local cuisine, a fine arts and crafts fair, educational lectures, culinary programs, children’s activities, live music, a road race and the annual Oyster Shuck-Off competition. Tickets are $35 per person. 

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