October on the Cape! If you’re not slurping oysters or hoisting a pint, you’re face-to-face with pumpkin people or hearing haunted tales about local spirits. While you’re out leaf-peeping, keep an eye out for these seasonally festive events.
1. Vinegrass Music Festival - Sunday, October 1
Does sipping wine while reveling in Americana bluegrass and folk music sound like a good time? Then this music festival will be your perfect autumn day. The boot-stomping fun at Truro Vineyards showcases American Roots live music from such bands as Monica Rizzio, The Last Revel, Twisted Pine and The High Hawks. Bring a beach chair or blanket to enjoy the show; the Crush Pad Food Truck, Truro Vineyards libations and Lewis Bros Ice Cream will be available on site. Advance tickets are required - and the show is rain or shine!
2. Yarmouth Seaside Festival - Saturday, October 7 through Monday, October 9
A longtime fall tradition on the Cape, this seaside fest features food vendors, a 5k race, 125+ artists and crafters, live music, a kayak and canoe race, sand sculpture contests, carnival rides and a fireworks display on Sunday night over Seagull Beach. Showcase your artistic talent at the Family Chalk Fest in the Bass River/Smuggler’s Beach parking lot!
3. Pumpkin Day at Bourne Farm- Saturday, October 7
Bourne Farm’s annual celebration pays homage to all things fall. From harvest-time classics like pick-your-own pumpkins and horse-drawn hayrides to fairground favorites like face painting and a petting zoo, there’s something for everyone to enjoy.
4. Wellfleet OysterFest - Saturday, October 14 and Sunday, October 15
The town of Wellfleet’s famous oysters are the star of the show at this annual celebration! In addition to food, there are tastings, cooking demos and special menus all around town, while artisan vendors, live music, a town spelling bee, and the jam-packed schedule of family events showcase quirky, beautiful Wellfleet in all its glory. The centerpiece of the festival is the heated Shuck Off competition. If you hadn’t already heard, this is one for your Cape Cod bucket list.
5. Pumpkin People in the Park - Friday, October 14 through Monday, October 31
You never know what you will find in Chatham’s Kate Gould Park—Friday evening summer band concerts are a given, but colorful little sharks, snowmen, and the Easter bunny have also been spotted creeping along its path. Starting soon, Pumpkin People make their return, and they get more inventive every year. Look closely at those three little pigs, that lobster giant, or the huge-scale rendering of Edward Munch’s The Scream to see the gourd as you’ve never seen it before.
6. Chatham Oktoberfest - Saturday, October 21
After snapping selfies with the Pumpkin People in the Park, stay put at Kate Gould Park on October 21 for the always festive Oktoberfest. Raise a toast to fall at the traditional beer garden, nosh on German food, enjoy authentic German music, browse local artisan vendors, and keep the kids entertained with pumpkin decorating and other fun games.
7. Sandwich Pumpkin Fest – Saturday, October 21
This pumpkin patch is like nothing you’ve ever experienced...it’s made entirely out of glass. Peruse beautiful, handblown glass pumpkins in a sea of autumn hues, each one expertly created by local and national artisans. All of the unique pumpkins on display are available for purchase; the perfect way to spice up your fall décor!
8. Halloween at Falmouth Museums on the Green - Saturday, October 21 and Friday, October 27
Travel through the centuries at the Falmouth Museums on the Green's "Sins, Sips, and Secrets" (Saturday, October 21). Designed for history-lovers, this interactive tour of the 1790 Dr. Francis Wicks House offers mild chills and fascinating insights into Falmouth’s nefarious and unearthly history, including spirits in times past. The following week, the Museums on the Green offer a more kid-friendly Halloween event "Wicked on Wicks" (Friday, October 27), which includes trick-or-treating at several historic properties on the campus, pumpkin painting, storytelling and a costume parade.
9. Halloween in Provincetown - Friday, October 27 through Sunday, October 29
A quintessentially ghoulish New England Halloween awaits as Provincetown hosts a monstrous medley of parties, dances, a haunted house, costume ball and more.
