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Fall Preview: Autumn Adventures Across Columbia County

2025 Corn Maze

As fall descends upon the Hudson Valley, Columbia County’s calendar fills with seasonal festivals, live music, family outings and opportunities to experience the changing landscape. From jazz and independent film to antiques and outdoor adventures, the weeks ahead offer plenty of reasons to explore.

A photograph from “Fall Preview: Autumn Adventures Across Columbia County”

The season begins Saturday and Sunday, Sept. 26th and 27th, as the Taconic Antiques Fair returns to the Columbia County Fairgrounds in Chatham. Dealers from throughout the region will fill the fairgrounds with furniture, art, textiles, clothing, jewelry and decorative objects representing a range of periods and styles. The fair is open from 9am to 5pm Saturday and 10am to 4pm Sunday.

October opens with a full weekend of events in Hudson.

The Hudson Jazz Festival takes place Friday through Sunday, Oct. 2nd – 4th, with three mainstage performances at Hudson Hall and additional pop-up performances planned around the city. This year’s mainstage lineup features Grammy-winning Cuban drummer and composer Dafnis Prieto, vocalist Vuyo Sotashe with pianist Chris Pattishall and vocalist Shenel Johns.

A photograph from “Fall Preview: Autumn Adventures Across Columbia County”

On Saturday, Oct. 3rd, the FASNY Museum of Firefighting hosts Dalmatian Day, a free family event celebrating the longstanding connection between Dalmatians and the fire service. From 10am to 3pm, visitors can meet live Dalmatians, enjoy games and children’s activities, watch a fire truck parade and learn about fire safety through the museum’s interactive Safety House.

A photograph from “Fall Preview: Autumn Adventures Across Columbia County”

Later that day, Hudson Oktoberfest returns to Upper Depot Brewing Co. from noon to 8pm.

A photograph from “Fall Preview: Autumn Adventures Across Columbia County”

The rain-or-shine celebration features live music, regional craft beer, wine and cider, local food, makers, games and family activities. Well-behaved dogs are also welcome.

The following weekend, collectors and transportation enthusiasts will gather at Copake Auction Inc. for its 34th Annual Bicycle & Automobilia Auction on Saturday, Oct. 10th. Beginning at 9am, the auction will feature rare bicycles, early motoring artifacts, signs, parts and transportation-related collectibles gathered from across the country. Auction previews will be held Thursday and Friday, with a swap meet opening Friday at 7am.

A photograph from “Fall Preview: Autumn Adventures Across Columbia County”

From Friday, Oct. 16th, through Sunday, Oct. 25th, FilmColumbia26 brings 10 days of independent and international cinema to Chatham. Presented by the Crandell Theatre, the festival is known for screening many of the year’s anticipated American and international films before their wider theatrical release.

A photograph from “Fall Preview: Autumn Adventures Across Columbia County”

For a classic fall outing, head to Samascott’s Garden Market in Kinderhook, where the annual corn maze remains open daily throughout September and October.

2025 Corn Maze
2025 Corn Maze

This year’s seven-acre maze is inspired by sunflowers and includes eight hidden stations along its winding paths. Visitors who find all eight receive a free small soft-serve ice cream or $1 off a hard ice cream.

The maze generally takes at least 60 to 90 minutes to complete. Because it is a working cornfield with mud and uneven ground, sturdy sneakers or boots are recommended. Entry begins at 11am, with the final entry at 4pm.

Fall can also be seen from a different perspective at Catamount Mountain Resort in Hillsdale.

A photograph from “Fall Preview: Autumn Adventures Across Columbia County”

The mountain’s Aerial Adventure Park, CataMonster Zip Tour and scenic chairlift rides continue on weekends through the fall season. Visitors can navigate elevated bridges and obstacles in the forest canopy, travel along North America’s longest dual-span zipline or ride to the summit for views across the Berkshires and Hudson Valley.

Whether the day calls for live music in Hudson, antiques in Chatham, a corn maze in Kinderhook or fall foliage from a mountaintop, autumn offers another chance to experience Columbia County from a new perspective.

Event dates, schedules and availability are subject to change. Check with each venue before traveling.

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The cover photograph of “Columbia County Celebrates America 250”

Columbia County Celebrates America 250

Columbia County will mark America’s 250th anniversary with three days of history brought to life by master storyteller Jonathan Kruk. Presented in period costume, the interactive, family-friendly performances will explore