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. Mashpee Oktoberfest - Saturday, October 4
This annual celebration on the green at Mashpee Commons pays homage to all things fall. Peruse 50 unique artisan and vendor booths, while enjoying live entertainment and craft beverages in the Biergarten. From harvest-time classics like pumpkin decorating to fairground favorites like face painting and food trucks, there is something for everyone. 

2. Vinegrass Music Festival - Sunday, October 5
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 performers as Bronwyn Keith-Hynes, The Cody Sisters, Rucksack Revolution and Monica Rizzio’s Roundup. 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!

3. Sandwich Glass Museum Pumpkin Fest – Saturday, October 11 and Sunday, October 12
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 at the Sandwich Glass Museum, 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!

4. Yarmouth Seaside Festival - Saturday, October 11 through Monday, October 13
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!

5. Outermost Roots & Blues Festival - Saturday, October 11 and Sunday, October 12
Bring your dancing shoes to this festival, because you’ll need them as you groove to the sounds of headliners like G. Love & Special Sauce, Steel Pulse, Mihali, Robert Randolph, Little Stranger, Ron Artis II, and Cedric Burnside. The perfect complement to the top-tier line-up of performers is the festival’s location: Nauset Beach in Orleans. Also enjoy a vibrant mercantile featuring local vendors, food trucks and a dedicated kids’ zone.

6. Wellfleet OysterFest - Saturday, October 18 and Sunday, October 19
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.

7. Pumpkin People in the Park - October 10 through 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.

8. Chatham Oktoberfest - Saturday, October 18
After snapping selfies with the Pumpkin People in the Park, stay put at Kate Gould Park on Saturday, October 18 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.

9. Wicked at Wicks at Falmouth Museums on the Green - Friday, October 24
The Museums on the Green offer this kid-friendly Halloween event, which includes trick-or-treating at several historic properties on the campus, pumpkin painting, storytelling and a costume parade. Learn about local history, including stories about Halloween in Falmouth in years past. 

10. Spooky Bear Halloween in Provincetown - Thursday, October 30 through Sunday, November 2
A quintessentially ghoulish New England Halloween awaits as Provincetown hosts a monstrous medley of parties, dances, a haunted house, costume ball and more.