Year-round and second-home owners alike know that autumn is unmissable in the area we serve. While our incredible foliage makes even your daily commute an exciting event, our local hotspots are alight with special fall programming! Our New York agents have weighed in with their decades of expertise in the area to give you a list of 7 can’t-miss things to do in Columbia County this season, updated for 2026.
1. Visit The Crandell for FilmColumbia
The Crandell Theatre in Chatham is a historic piece of art that underwent $4 million in renovations in 2025. The theatre’s team has focused on bringing the theatre back to its 1927 Spanish Renaissance-style glory while incorporating updates to the technology behind screening their carefully-curated selection of movies.
Besides their year-round offerings, ranging from blockbusters, to indie films, to beloved classics, people flock to The Crandell for FilmColumbia. The 10-day festival gives film fanatics the opportunity to see the next award-winning indie film before the rest of the country catches onto the hype.
2026 is the 26th year of the festival, which will occur from October 16th to October 25th. FilmColumbia is known for their incredible special events and guest speakers; this year, they're honoring Chatham's own Jane Schoenbrun, a writer and director. Jane's film Teenage Sex and Death at Camp Miasma has been the indie hit of the summer, but you may also know them from the indie horror I Saw The TV Glow or for directing the music video for Night Shift by Lucy Dacus.
2. Dress up for FlannelFest at Chatham Berry Farm
Visiting the Greenhouse Cidery and food pop-up Yummy Kitchen at Chatham Berry Farm is always a great time (their outdoor fires make it a great place to spend the evening all the way through November!), but the farm really packs a punch for FlannelFest.
On Saturday, October 10th, Chatham Berry Farm invites you, your kids, and even your pets to don their favorite flannels and celebrate the fall season. The event is free, but FlannelFest asks you to consider coming with a contribution for their pet food drive to benefit the Columbia Greene Humane Society. From 12pm-9pm, you can enjoy live music, cream puffs, and soft serve alongside the usual tasty ciders and Yummy Kitchen’s asian-inspired bites.
3. Watch classic horror movies at the Spotlight of Hudson
What’s October without some chills and thrills? After seeing the next best thing at FilmColumbia, you can head to Spotlight of Hudson for their masterfully curated Halloween events. Besides showing new releases (like the on-theme Practical Magic 2), their “Five Dollar Frights” series shows familiar favorites for cheap. So far, they’ve announced showings of Beetlejuice, Clue, The Shining, and more!
4. Take a Scenic Hike in the Hudson Valley
We have no shortage of beautiful trails that are free to explore in the area. Some of our agents’ favorites include:
Ooms Conservation Area
This park, located just outside of the village of Chatham, is perfect for those seeking an easier hike with stunning views. Ooms contains 3 miles of trail loops within 180 acres, complete with lots of places to sit, rolling grasslands, and Sutherland Pond.
High Falls Conservation Area
You can visit Columbia County’s highest waterfall by taking a short, about half-mile trail into the woods in Philmont. This is a popular hike that is well-marked and relatively flat, so you’re bound to run into your neighbors of all ages at this hotspot!
Harvey Mountain State Forest
For those seeking a more moderate hike, there are plenty of trails in Austerlitz's Harvey Mountain to explore. There are a variety of ways to hike up to the top–most are estimated to take you around 2 hours on average.
In addition to walking paths, Harvey Mountain and Beebe Hill combined offer 30 miles of trails suitable for anything from biking to camping to horseback riding and more!
5. Visit the best farms and farmstands in Columbia County
Many of the beautiful, sprawling farmlands you pass in Columbia County have farmstands and events that welcome the public, and are especially great for families seeking their next autumn tradition! We asked our agents to narrow down to just a few of their favorites:
Woodlife Farm in New Lebanon
Woodlife Farm has something for you to enjoy no matter the season, and we encourage you to come hungry. You can eat right at their market, or pick up locally-sourced groceries to stock up your kitchen at home. Woodlife is famous for their bourbon barrel-aged syrup!
Woodlife encourages patrons to spend the day enjoying all the farm has to offer. You can take part in their seasonal pick-your-own offerings of flowers, produce and Christmas trees. They even bring in outside entertainment throughout the year, including live music, fitness classes, car shows, special theme dinners and more!
Golden Harvest Farm in Valatie
Our team cites Golden Harvest Farm’s roadstand as their go-to for picking up apples, cider donuts, mums, pumpkins, and other fall delights.
If you have more time than a quick grocery run, we’d recommend stopping into the Harvest Spirits distillery–on Fridays, you can enjoy live music alongside their ciders, beers, spirits and mocktails. While the distillery is open year-round, the farm’s smoke house is typically open from May to November.
Samascott’s Orchard & Garden Market in Kinderhook
Samascott’s Orchard is about a mile away from their Garden Market, and each hotspot has its own unique offerings.
At the orchard, their pick-your-own offerings expand far past the traditional apples and pumpkins: in the fall, you can also find plums, pears, strawberries, grapes, broccoli, kale, tomatoes, squash, peppers and much more! Just stop in or check their website to find out what’s currently available. If you’re planning a group outing, you can even rent special orchard bikes that can seat 4-6 people, and have crates attached to carry your bounty around the farm.
Most of Samascott’s scheduled events take place at the garden market. The farm will bring in food trucks, maker markets, and is famous for their intricate corn mazes that feature a different design each year. Inside the market and greenhouse, you’ll find everything from flowers to prepared foods, to fresh produce, to nonperishables and more–including their 100% pure apple syrup.
Our agents recommend making a stop on your Electric Trail bike ride (which runs behind the market) to try out the garden market’s homemade ice cream!
6. Bring the family to kid-friendly fall festivities
While most of our selection is appropriate for all ages, our agents have a few favorites in mind for entertaining younger kids:
Hawthorne Valley’s Fall Festival
You can visit Hawthorne Valley in Ghent for their annual Harvest Festival on Saturday, October 10.
The festival combines fun with opportunities to learn more about biodiversity and agriculture. Some of the classic fall activities offered include hay rides, horse rides, and cider pressing. You can also stop by the farm store’s demo tent to chat with local vendors and enjoy samples of their wares.
Everyone in the family is bound to enjoy their selection of live music, but kids will love the marionette performance by The Magical Puppet Tree!
Trunk or Treat Events in Columbia County NY
We sell lots of homes in Columbia County whose primary appeal is privacy. But lack of neighbors makes for poor trick-or-treating! Here are a few trunk-or-treat options for your little ones around the county:
Taconic State Park- Copake Falls/Rudd Pond in Copake:
Saturday, October 17 from 4 p.m. to 6 p.m.
FASNY Museum of Firefighting in Hudson:
Saturday, October 24 from 10 a.m. to 12 p.m.
American Cruisers Chapter 123 and VFW Auxiliary 7765's: 30 Elizabeth St, Red Hook
Saturday, October 24 from 12 p.m. to 2 p.m.
7. Tour the Ichabod Crane Schoolhouse in Kinderhook
Take a historical tour that’s perfect for the Halloween season! The current schoolhouse dates to about 1850, but an earlier school on the same site was home to schoolmaster Jesse Merwin. Merwin was a lifelong friend of the writer Washington Irving, and is cited as the inspiration behind the school headmaster Ichabod Crane in “The Legend of Sleepy Hollow.”
While Irving spent most of his life in and around New York City, he drew inspiration from his travels in the Catskills and along the Hudson River for lots of his stories, including Rip Van Winkle!
If you're seeking a Columbia County home to call your own, don't hesitate to get in touch. Our agents would love to guide you into a lifestyle that suits you in every season!
