What’s On in the Hudson Valley & Catskills This October
Fall has arrived, and October’s calendar across the Hudson Valley and Catskills is full of good reasons to get out: antiques in Rhinebeck, films in Woodstock and Chatham, art and music in Kingston, and a festival devoted entirely to pickles. Here are the dates we’ve got marked.
The Country Living Fair
October 2-4 · Rhinebeck
Antiques, independent makers and plenty of ideas for the house take over the Dutchess County Fairgrounds for three days. With more than 200 vendors alongside workshops, speakers and music, it’s one to give yourself time to browse.
Catskill Food Festival
October 3 · Catskill
Food trucks and local vendors take over Dutchman’s Landing Park beside the Hudson, with live music and artisan stalls to browse between bites. The festival runs from noon to 6pm.
Hudson Oktoberfest
October 3 · Hudson
Regional beer, wine and cider, live bands, food and local makers fill the day at Upper Depot Brewing Company. This year’s event also supports local animal shelters and rescue organisations.
Robibero Grape Stomping Festival
October 3-4 · New Paltz
Grape stomping is the main event at Robibero Winery, with wine, live music, wood-fired pizza, lawn games and bonfires filling out the afternoon. It runs from 11am to 6pm on both days, and children under 12 can join the stomping for free.
Colors in the Catskills
October 3-4, 10-11 and 17-18 · Hunter
The Hunter Mountain tradition formerly known as Oktoberfest has a new name and three themed weekends. It begins with First Leaves, turns to Oktoberfest on October 10–11, then finishes with a costume weekend. There’s live music, food, local vendors and the option to take the Scenic SkyRide for a better look at the mountains.
Belleayre Fall Festival
October 3-4 and 10-11 · Highmount
Local artists and makers come to the mountain alongside live music, food and scenic gondola rides. There’s a craft fair, winter apparel sale and activities for children, including a pumpkin patch. Admission and parking are free.
Highlands Cup Horse Show
October 9-11 · Amenia
The Highlands Cup brings international show jumping to Amenia, alongside food, art and family activities. Saturday’s Major League Show Jumping team competition and Sunday’s Grand Prix are the headline events. Even if you don’t usually follow equestrian sport, it’s a rather good setting in which to discover it.
O+ Festival
October 9-11 · Kingston
For three days, O+ fills Kingston with music, public art, performances and wellness events. The festival also supports healthcare access for participating artists and musicians through an exchange with local health practitioners.
Hawthorne Valley Harvest Festival
October 10 · Ghent
A day on the farm with cider pressing, hayrides, live music, food and the Roots & Relics Market. There’s a pie contest, guided walks and activities for children too. The festival runs from 11am to 3pm, and admission is free.
Windham’s Autumn Affair
October 10–11 · Windham
Windham’s Main Street fills with local makers, food, live music and family activities for its annual Autumn Affair. It’s a good one for wandering between stalls, then spending a little more time exploring the town. The event runs from 10am to 5pm on both days.
Woodstock Film Festival
October 14-18 · Woodstock and surrounding towns
The festival spreads well beyond Woodstock, with screenings and events in Saugerties, Kingston and Rosendale too. Pick a film or two, leave room for an unplanned stop afterwards, and make an evening of it.
Catskills Comedy Festival
October 16-18 · Catskill
A newer addition to the autumn calendar, the Catskills Comedy Festival brings stand-up, performances and workshops to venues around the village. Check the programme for a show that catches your eye, then stay for dinner.
FilmColumbia
October 16-25 · Chatham
Keep the filmgoing going at Chatham’s Crandell Theatre, where FilmColumbia screens upcoming American and international films over ten days. Look out for the Saturday Sneak, a preview screening whose title isn’t revealed until the audience is seated.
New York State Sheep & Wool Festival
October 17-18 · Rhinebeck
The festival returns to the Dutchess County Fairgrounds with animals, fibre arts, demonstrations, workshops and a great deal of beautiful wool. You don’t need to know how to knit to enjoy a day here, though you may leave wanting to learn. For a closer look at the sheep, the makers and this year’s program, read our guide to the Rhinebeck Sheep & Wool Festival.
Beacon Sloop Club Pumpkin Festival
October 18 · Beacon
This free festival takes place beside the Hudson at Pete and Toshi Seeger Riverfront Park. Expect pumpkins, homemade pie, cider and live music on two solar-powered stages. Make time for a walk by the water while you’re there.
Rosendale International Pickle Festival
October 18 · Ulster County Fairgrounds, New Paltz
Yes, an entire festival for pickles. Despite its name, the event takes place at the Ulster County Fairgrounds in New Paltz, with more than 100 vendors selling pickles, food and handmade goods. There’s a home pickling contest and a Pickle Triathlon involving eating, juice drinking and tossing. Bring cash for admission at the gate.
