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 3
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 4
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 Sam Grisman Project, East Nash Grass, The Casitas and Dan Sturgis. 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. Fall Festival at Taylor-Bray Farm - Saturday, October 10
Taylor-Bray Farm’s annual Fall Fest brings classic autumn fun to the historic Yarmouth Port farm. Enjoy hayrides along the Don McIntyre Trail, old-fashioned games, pumpkins and gourds, apple cider and cider donut holes, plus visits with the farm’s beloved animals.

4. Sandwich Glass Museum Pumpkin Fest – Saturday, October 10 and Sunday, October 11
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!

5. Yarmouth Seaside Festival - Saturday, October 10 through Monday, October 12
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!

6. Outermost Roots & Blues Festival - Saturday, October 10
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, Digable Plants, Grateful Dub and Ron Artis II. 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.

7. Wellfleet OysterFest - Saturday, October 17 and Sunday, October 18
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.

8. Pumpkin People in the Park - October 12 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.

9. Chatham Oktoberfest - Saturday, October 17
After snapping selfies with the Pumpkin People in the Park, stay put at Kate Gould Park on Saturday, October 17 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.

10. Haunted Hallows at Mashpee Commons - October 9-31 (Fridays and Saturdays)
Spooky season comes to life at Mashpee Commons! Starting October 9, brave souls can take on Haunted Hallows, a 30-minute walk-through haunted attraction happening Friday and Saturday evenings through October 31 (buy tix in advance). Pair the scares with a stop at Halloweentown for local vendors, food trucks, cider and the Naukabout Beer Garden, then return October 26 for the annual Halloween Party, complete with trick-or-treating and a costume parade for kids and pups.

11. Spooky Bear Halloween in Provincetown - Thursday, October 29 through Sunday, November 1
A quintessentially ghoulish New England Halloween awaits as Provincetown hosts a monstrous medley of parties, dances, a haunted house, costume ball and more.

12. Haunted Halloween Around The Common - October 31
This Halloween, head to the Edward Gorey House in Yarmouth Port for frights, delights and a thoroughly unsettling good time. From 4 to 7:30 p.m., Gorey House and its neighbors around the Common—including Captain Bangs Hallett House, Thacher Hall, Chapter House Inn, Yarmouth Port Library and the Historical Society of Old Yarmouth—invite you to join the haunted hullaballoo. Enjoy free admission, trick-or-treating, Gorey tarot readings and plenty of Halloween fun. Costumes encouraged; candy guaranteed.