Tis’ the season for sweet apple cider, cozy sweaters, and fun weekends in the cool country air… September and October bring Fall fun for everyone in the Sullivan Catskills. Whether you’re traveling solo or bringing your tribe, the Sullivan Catskills is a leaf-peepers dream come true. From festivals to pumpkin parties, there’s a variety of events coming up you don’t want to miss! Book a room, pack your bags – we’re waiting for you.

16 Ways to Have Fun this Fall in the Sullivan Catskills

Sullivan Catskills Farm to Table Week
September 20-29
A celebration of our local farmers, chefs, distillers, brewers, wine and cider makers – 11+ eateries in the Sullivan Catskills will pay homage to the local bounty of our Catskills region. Learn more, make a reservation – your taste buds will thank you!

Hilly Acres Farm Fest
Saturday, September 21 • 11am-4pm
Meet the animals and the farmers – admission is free at Hilly Acres Farm Fest! Take a hayride or test your strength with a hay bale toss. Feast on delicious local food while enjoying live music. Shop local craft and food vendors and decorate a pumpkin. You can even learn how to make butter.

The Farmhouse Project’s Terrain & Table
Saturday, September 21 • 4-8pm
Enjoy a sumptuous family-style seasonal spread, made from local farm-fresh ingredients and global flavors. This is the fourth dinner in The Farmhouse Project’s Terrain & Table Dinner Series. Imagine a beautiful tablescape, seats for 100+, and the most lovely outdoor setting where you’ll meet friends new and old from near and far. This dinner will be held at SUNY Sullivan’s Hope Farm with chef Cheryl Perry from Red Barn Studio and forager Laura Silverman of The Outside Institute.

The Harvest Festival at Bethel Woods
Sundays, September 21 & 28 • 11am-4pm
The Harvest Festival highlights the bounty and talent of the Sullivan Catskills and the surrounding region. This free, family-friendly festival features 100+ vendors, including a farmer’s market, craft and artisan goods, specialty food, beer, wine, spirits, and food trucks. Plus, live music, a creative learning tent, and corn and hay mazes.

Roscoe Beer Co. Oktoberfest
Saturday, September 28 • 11am-7pm
Feast on authentic German fare and craft beer at the 5th Annual Oktoberfest at Roscoe Beer Co. This family-friendly event features pumpkin painting and a hay maze for the kiddos and a pumpkin carving station for the adults. Listen to live music as you shop local vendors or watch the live wood carving show. Dress up is encouraged so sport your best Oktoberfest themed costume to take part in the contest.

Narrowsburg Honeybee Fest
Saturday, September 28 • 11am-5pm
Food, honey, fun! That’s what you find at the 5th Annual Narrowsburg Honeybee Fest. Stroll down Main Street, shop for local honey and artisan crafts. Watch the beekeepers do a live honey extraction. Learn all about bees and why they’re the world’s most important pollinator.

National Alpaca Day at Buck Brook Alpacas
Saturday, September 28 • 12-4pm
Celebrate National Alpaca Day at Buck Brook Alpacas. Take a farm tour, watch spinning and weaving demonstrations, shop for a variety of fiber crafts. This family-friendly event will leave you posting the cutest alpaca selfies.

8th Annual Wine Festival at Bethel Woods
Saturday, October 5 • 1-5pm
Raise your glass to some of the finest wines in the Hudson Valley and Finger Lake regions while listening to live music, participating in fun games, and enjoying a food court to satisfy all cravings. The 8th Annual Wine Festival at Bethel Woods is the perfect excuse to get away with your girlfriends or partner. Upgrade to the VIP Experience for early entry into the festival, access to the VIP lounge, an exclusive 6-course wine and food pairing, a commemorative tasting glass and free admission to The Museum.

Monster Mash Murder Mystery Dinner at Burn Brae Mansion
Saturday, October 5 • 6-9pm
Be part of a classic whodunnit at Burn Brae Mansion’s Monster Mash Murder Mystery Dinner. You can even spend the night but beware… Burn Brae Mansion has been the subject of numerous paranormal investigations. Horror movie icon, Linda Blair of The Exorcist, says it’s one of her favorite places to stay when visiting the area.

34th Annual Giant Pumpkin Party
Saturday, October 5 • 9-4pm
Bring the kids to the 34th Annual Giant Pumpkin Party and Children’s Parade. The costume parade kicks off at 9am followed by food, crafts, games, pumpkin decorating, pony rides, mini-golf, hay bale throwing contests, a baking contest, and much more.

Rocky Horror Picture Show Live at Forestburgh Playhouse
Select Friday’s & Saturday’s in October • 7:30pm
Do the time warp again! See the Rocky Horror Picture Show performed live at The Forestburgh Playhouse. This cult classic encourages dress up and audience participation – so no need to be shy. Through elaborate dances and song, you’ll be tapping your feet and yelling “oh, Brad”! Enjoy dinner and cocktails before the show and make a night of it!

7th Annual Craft: Beer, Spirits, Food Festival at Bethel Woods
Saturday, October 12 • 1-5pm
Beer, spirits, cider, and mead await you at the 7th Annual Craft: Beer, Spirits, Food Festival at Bethel Woods. Crafted from beverage makers across the region, this is one fun event! Enjoy live music, a variety of food and artisan vendors. Upgrade to the VIP Experience for early entry into the festival, access to the VIP lounge, an exclusive dining session, a VIP tasting glass, a complimentary gift and free admission to The Museum.

Callicoon Art Walk
Saturday, October 12 • 12-8pm
Witness the growing art and music scene in the picturesque hamlet of Callicoon. The Callicoon Art Walk features art in storefronts and public spaces with performances and workshops throughout the day. In the evening, video projections will light up the town. Shop the Main Street merchants; eat and drink at the local bars and restaurants.

Barryville Pumpkin Fest
Saturday, October 12 • 12-5pm
In its 16th year, the Barryville Pumpkin Fest celebrates art, food, and fun. Adults, kids, and pets are encouraged to wear costumes and participate in the contest. If baking is your specialty, enter the sweet or savory bake-off. You even have the chance to win prizes with a pumpkin carving contest and scarecrow design contest. At the end of the day, take part or witness the annual pie-eating contest.

Dark Forest Fright Walks at Burn Brae Mansion
October 12, 18, 19
Part of New York’s Haunted History Trail, Burn Brae Mansion welcomes all to their Dark Forest Fright Walks. Enjoy libations and food while shopping for crafts and Halloween items too. Please note, the Fright Walk is not recommended for small children and does require trail walking.

Winterton Farms 4th Annual Artisan & Harvest Festival
Sunday, October 13 • 11am-5pm
Celebrate the crisp days of Autumn at Winterton Farm’s 4th Annual Artisan & Harvest Festival. Take the kids on a wagon ride, shop for local handmade crafts, feast on savory and sweet treats. There’s live music, demonstrations, and free admission too!