Happy Fall Y’all! The days are getting shorter, the air a bit cooler, and very soon our Insta-worthy Fall foliage will emerge. From lavish foodie festivals to pumpkin festivals, here are 13 ways to experience October in the Sullivan Catskills. Grab your calendar, reserve a room and escape for the weekend – we’re waiting for you.

13 Ways to Experience October in the Sullivan Catskills

Catskills Wine & Food Festival

Saturday & Sunday, October 6 & 7 • 11am-11pm
Shaping up to be the most talked about event of the season, the first annual Catskills Food and Wine Festival is nestled in the beautiful mountains of the Sullivan Catskills and sprawled across a magnificent campground. Festival-goers will be treated to an experience like no other – celebrity chefs, cooking demos, private tastings, a dynamic selection of libations and performances by Lord Huron, The Revivalists, and Escort (just to name a few). Gather your tribe, get your tickets and make a weekend out of it.

Wine Festival at Bethel Woods

Saturday, October 6 • 1-5pm
Savor the finest wines from 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. And this year, Bethel Woods added a few unique interactive activities – including a paint & sip session, providing the perfect hand-crafted souvenir to take home.

Callicoon Art Walk

Saturday, October 6 • 12-8pm
The Callicoon Art Walk showcases the growing art, music and retail community in the hamlet of Callicoon on the Delaware. Imagine video projections, outdoor art installations, live music, vendors, a pub crawl, free art workshops, and more.

Murder Mystery Dinner: The Quick and the Dead

Saturday, October 6 • 6-9pm
The Tombstone Gunfighters have come together to perform their Western Days show at the Victorian Burn Brae Mansion. But for one Wild West wannabee, this will be the last draw. Help solve the crime and win some great prizes. Tickets sell fast, so reserve asap.

Barryville Pumpkin Fest

Saturday, October 6 • 10am-5pm
Start this free, fun-filled day of art, food, and fun with a live DJ Halloween Jam. Enter your best sweet or savory creation into the pumpkin bakeoff or sign up for the pie eating contest. If you’re crafty with pumpkin carving/decorating or scarecrow making, there’s a contest for you too! And of course, there will be a costume contest for adults, kids, and pets – so be sure to get everyone dressed up.

Giant Pumpkin Party & Children’s Parade

Saturday, October 6 • 9am-4pm
Begin the morning at the Daniel Pierce Library to watch the parade. Then, head to the fairgrounds where the day of fun begins… games, pumpkin decorating, crafts, bouncy houses, a haunted house, great food and more! Plus, the kids can participate in the annual Costume March and enjoy a free book to take home.

Legends in the Sky Stargazing Party

Sunday, October 7 • 6:30pm
Sit fireside and cuddle up under a blanket with hot cocoa in hand, under the night sky at Bethel Woods Center for the Arts. Astronomy fun for everyone awaits… Listen to heroic legends past and present, learn astronomy facts, stargaze, and then create our own constellations from family myths and your hopes for the future.

The Rocky Horror Picture Show – Live on Stage

Weekends, October 12-27
Let’s do the time warp again – live at the Forestburgh Playhouse! In this cult classic, sweethearts Brad and Janet stuck with a flat tire during a storm, discover the eerie mansion of Dr. Frank-N-Furter, a transvestite scientist. As their innocence is lost, Brad and Janet meet a houseful of wild characters, including a rocking biker and a creepy butler. Through elaborate dances and rock songs, Frank-N-Furter unveils his latest creation: a muscular man named “Rocky”. Dress in character for added fun.

Halloween Weekends

October 12-14, 19-21, 26-28
Take the family on a Fall retreat to Frost Valley YMCA. Make Halloween exciting with pumpkin painting, Halloween crafts, and apple cider making. Bring your costumes for a costume party and if you dare, walk the haunted trail. With additional outdoor activities throughout the weekend, everyone is sure to have a blast.

Craft: Beer, Spirits & Food Festival at Bethel Woods

Saturday, October 13 • 1-5pm
Quench your thirst with a variety of beer, spirits, cider, and mead brought to you from craft beverage makers across the region. Enjoy festival food, shop artisan wares – there will be 90+ vendors to explore on the grounds of Bethel Woods Center for the Arts. Plus, the Spin Doctors will be playing live – fun for everyone over 21!

Halloween Festival

Saturday, October 13 & 20 • 7-10pm | Friday, October 19 • 7-10pm
Are you brave enough to take the Fright Walk on the grounds of the haunted Burn Brae Mansion? If you make it through, enjoy some Shrewd Fox Brewery beer and cider along with food and craft vendors at this spooktacular Halloween Festival.

Classes at Henning’s Local

Saturday, October 13 • 12-3pm • Pies for Fall & Holidays
Wednesday, October 17 • 6:30-8pm • Knife Sharpening Clinic
Saturday, October 27 • 10am-2pm • The Need to Knead
Henning’s Local hosts a variety of special hands-on, intensive workshops taught by local chef and educator, Cheryl Perry of Red Barn Studio. Classes are hands-on and offer interactive, educational experiences, knowledge, and techniques that can be used at home – a perfect experience to add to your time spent in the Sullivan Catskills.

Marathons & 5K Runs

If staying active on your visit is of most importance, take part in one of the 5K’s happening this month. On Saturday, October 6 at 10am, prior to the Wine Festival at Bethel Woods, be part of the Vintage Runs Half Marathon and 5K. The following weekend, Saturday, October 13 from 10:30am to 1:30pm, start the day at Catskill Brewery and enjoy the Fall foliage on the Livingston Manor Half Marathon & 5K Run/Walk. Lastly, throw on those costumes and get festive for the Halloween season, join in at the Monster Dash 5K Walk/Run at the Town of Thompson Park on Saturday, October 27 from 9am to 12pm.