Ivory clapboard farmhouse porch with bluestone steps, a dark oak door, and an amber-leaved maple beside an autumn lawn.

Explore Hillsdale and Copake Fall Events in October 2026

Starting October 1, Catamount opened the CataMonster ZipTour and its scenic chairlift on Fridays, 10 a.m. to 3 p.m., in addition to Saturdays and Sundays. From September 8 through 30, both rides ran on weekends only. The extra day lasts through November 1. The Aerial Adventure Park keeps its weekend schedule of 10 a.m. to 5:30 p.m. through the same date.

After November 1 the mountain goes quiet until ski season, but the Copake-Hillsdale Farmers Market has Saturdays scheduled through November 21. The Copake Grange has a musical running the two weekends before that. The mountain gets the foliage crowds. The rest of the season depends on a short list of vendors, volunteers and venues, and many of them turn up in more than one place on the calendar.

One Weekend Shows How Much Overlaps

The second weekend of October is when the overlap is easiest to see. Here is what's on the local calendar from Friday, October 9, through Sunday, October 11:

  1. Friday, October 9. The ZipTour and chairlift at Catamount, 78 Catamount Road, run 10 a.m. to 3 p.m. That evening Jack Grace plays Roe Jan Brewing Co. on Anthony Street in Hillsdale from 7 to 9 p.m. His songs mix rock with Latin influences.
  2. Saturday, October 10, morning. The farmers market opens at 9 a.m. at Roeliff Jansen Park, 9140 Route 22, and runs until 1 p.m.
  3. Saturday, October 10, midday. Taconic State Park holds its third annual Autumn in the Park from 10 a.m. to 3 p.m. at 253 Route 344 in Copake Falls. Admission is free. The schedule lists yard games, pumpkin painting, cider, apple games, food trucks, adoptable dogs from Hudson Paws, visits from Smokey Bear and live animals from the Reptile Adventure Program. Cider and pumpkins are available while supplies last.
  4. Saturday, October 10, evening. Duo Andalucia plays flamenco and jazz fusion at Roe Jan Brewing from 7 to 9 p.m.
  5. Sunday, October 11. Catamount's lifts run again. The Carol & Nick Duo plays an earlier set at the brewery, 5 to 7 p.m.

Roe Jan Brewing's regular hours line up with this kind of weekend. The taproom opens at noon on Fridays and Saturdays and stays open until 9 p.m. On Sundays it's open noon to 8 p.m. From Tuesday through Thursday it opens at 5 p.m., and it's closed Mondays. The Friday lift hours finish at 3 p.m., and the taproom has been open since noon.

The Market Supplies Food for Much of the Calendar

The farmers market's vendor list explains a lot of the overlap. Its 2026 lineup includes produce from Common Hands Farm, Earthborn Garden, Hawk Dance Farm and Markristo Farm. It also includes Pym Farm's grass-fed Red Devon beef, Coleman's Catch Seafood, and cider doughnuts made on site by Great Cape Baking Company. Some vendors on the list also cook for other events this fall.

Aloha Tacos is on the list as an Asian-inspired taco truck that comes on limited dates. On September 26 the same truck served at the Copake Grange's annual Square Dance and Ice Cream Social. Caller Lance Olds taught the dances, and Laura Murkowski and Vicky Boulay of the Bad Cats played.

Authentic Eats by Oleg is listed for Ukrainian and European-style prepared food, also on limited dates. On Friday, October 16, from 2 to 7 p.m., it holds a fall pop-up at the Copake General Store, 171 County Route 7A. The menu is handmade Eastern European comfort food, seasonal bites and sweets. That Friday is also a foliage-hours day at Catamount, so the lifts close an hour after the pop-up opens.

The market also accepts SNAP/EBT cards, and its season listing mentions music and family activities along with the food. It opens Saturday mornings from mid-May to late November. In fall it falls on the same Saturdays as most of the other local events.

A Painter's Year on the Rail Trail

In October, the most local thing to see indoors is the exhibit at the Roeliff Jansen Community Library, 9091 Route 22. "Rail Trail: The Power of Place" is a show of nine paintings by Peter N. Fritsch, on view through October 28 during library hours. The library says he painted them in 2025 and 2026. They follow the Harlem Valley Rail Trail in Columbia County through the seasons, from late-summer and autumn foliage to winter snow, early spring light and a November rain. The library's description says Fritsch draws on the Hudson River School. He leaves out the grand views of Frederic Church and Thomas Cole and paints a quieter landscape shaped by nature and by human history. Fritsch was born in New York City in 1954. He earned a BFA from the School of Visual Arts and later studied for three years at the Art Students League in Manhattan.

The trail he paints is still unfinished. The Harlem Valley Rail Trail Association says it took 37 years to build the current 26 miles, from Wassaic to the outskirts of Hillsdale. The group aims to raise the money within five years to finish the last 20 miles to the Village of Chatham. One phase of the plan is a Hillsdale section running to the Taconic State Parkway. The final step, which the association calls the Golden Spike, would join the two halves of the trail across the parkway. The association lists Dan Haas of Copake and Karen Budd of Hillsdale among its local leaders, with Phil Meeks as chair. The paintings show the trail as it is today, at its northern end, while the plan to extend it is still being funded.

Where to Eat Around the Calendar

The fall schedule passes by several kitchens that post current hours:

  • Random Harvest Market, Café & Community Space, 1785 Route 23, Craryville, describes itself as worker-owned. The market is open daily 8 a.m. to 7 p.m., and the café serves 8 a.m. to 3 p.m.
  • Zinnia's Dinette, 1843 Route 23, Craryville, posts dinner daily from 4 p.m. and lunch from 11:30 a.m. on Saturday, Sunday and Monday.
  • Dad's Copake Diner, 178 County Route 7A, opens at 7 a.m. and is closed Tuesdays. It closes at 8 p.m. most days and at 7 p.m. on Sundays.
  • The Greens at Copake Country Club, 44 Golf Course Road, Craryville, serves dinner Monday and Thursday. It opens at 11 a.m. Friday through Sunday and is closed Tuesday and Wednesday. Happy hour on weekends runs 2 to 4 p.m.
  • Cook & Larder, 2642 Route 23, Hillsdale, is owned by Anthony DeCaria. In summer 2025 it added a made-to-order menu and indoor and outdoor seating, according to a Berkshire Edge profile. Check its current hours before planning a stop.
  • Hillsdale House, 1 Anthony Street, serves tavern fare and brick-oven pizza with a full bar, on the same street as the brewery. The town's directory says to call or check its social media for current hours.

In Copake Falls, the Taconic Wayside Inn at 108 Route 344 is listed for sale on its own website. The site says the same family has owned and run it for more than 55 years and that it is ready for "new stewardship." It is on Route 344, the same road as the state park.

November, After the Lifts Stop

Catamount's foliage schedule ends Sunday, November 1. The calendar goes on without it. Two of Us Productions stages Man of La Mancha at the Copake Grange, 628 Empire Road, on Fridays and Saturdays, November 6, 7, 13 and 14, at 7:30 p.m. Sunday matinees are November 8 and 15 at 3 p.m. Tickets cost $20 for adults and $15 for youth 18 and under and seniors 60 and over. They're sold at the door, by phone at 518-329-6293, or through the company's website. The production is the 1965 musical based on Cervantes' Don Quixote, which won five Tony Awards, including Best Musical.

The farmers market's last Saturday is November 21, six days after the final matinee. The market opened its 2026 season on May 16.

Kyle has spent her life in this part of the valley and follows the small changes, like a vendor showing up at a new venue or a longtime inn going up for sale. If your fall plans in Hillsdale or Copake start to include a property of your own, Kyle Elizabeth Irwin would be glad to walk the roads with you, from Route 22 to the end of Route 344. Let's Connect.

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Her knowledge of the area and lifelong relationships perfectly intertwine to best serve the needs and interests of her community and those interested in making the Hudson Valley a part of their lives.

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