Encompassing a wide area stretching west of the Hudson River between Albany and New York, Ulster County is a fantastic destination for enjoying the wild forests, charming towns, and many rich and diverse events and activities of Upstate New York.

This area of the scenic Hudson Valley is defined by rural valleys, small towns, and wilderness preserves just over an hour north of New York City. As such, it is a popular fall destination for families and individuals wanting to experience something wild, rustic, traditional, old-fashioned, or artistic among the colorful leaves of the surrounding trees.

From music festivals and art displays to museums and guided hikes, Ulster County has something for everyone in the fall months. Read on to find out about some of the best events and things to do in Ulster County in the fall. 

Seeing The Fall Colours

A popular yearly pilgrimage takes place in the northeast every year as visitors, some from around the world, come to see the trees change their colors in the run up to winter. The landscapes of Ulster County - with its gently sweeping vistas and open valleys, make this a particularly great place to enjoy the vibrant fall palette.

We recommend taking the Ashokan Rail Trail (http://ashokanrailtrail.com/) to see the fall colors, as it skirts the Ashokan Reservoir along an old converted rail line. This trail is multi-use, being great for bikes and hiking parties large and small.

Being an old rail line, the route is even and great for any level of hiker, along with the wide variety of landscapes you’ll encounter.

Woodstock Film Festival

For a slightly more cultural affair there is the ever popular Woodstock Film Festival, held from the end of September through early October at multiple locations including Woodstock, Kingston, and Saugerites.

Between these three locations there will be approximately 150 films screened, including drive-in showings, short films, and live-streams. Added to this list are special events like discussion panels and Q&A sessions with filmmakers.

Check out the festival lineup, schedule, and information at their website:  https://woodstockfilmfestival.org/

Fall Family Fun Fest

The Fall Family Fun Fest will take place at the Ashokan Center south of the Ashokan Reservoir near Olivebridge. This family oriented event will include a range of fall activities including cider pressing, blacksmithing demonstrations and workshops, live music and food stands. 

Another highlight will be the guided tours and hikes operating from the festival. This event will be held (mostly) outdoors - so bring a chair and a blanket. Visit the website for more info: https://ashokancenter.org/product/fall-fest-2021/

Check Out Our Blog: The Best Ulster County Farms For Kids and Adults

Secret Ruin Hike on Overlook Mountain

For a (mildly) spooky outdoor adventure, the Born Wild travel company (https://www.bornwild.rocks/day-trips-2/secret-ruin-hike) offers guided hiking tours to visit the various ruin sites that dot Overlook Mountain in north Ulster County near Woodstock.

These ruins include an old house and hotel, as well as a visit to the Overlook Fire Tower for stunning panoramic views of the surrounding hills and valleys. There’s also a visit to Eagle Point lookout, which, fittingly, is a great place to spot local varieties of eagle.

The overall hike could be rated as moderate to easy, beginning at a trailhead north of the town of Woodstock, NY. The Secret Ruin hike runs most weekends in the fall and is a great way to get out and see the fall colors, as well as some historic sites and views that others might not experience.

Walktoberfest Farmers Market

This market fair is another event bringing together artists, craftspeople, and distributors of fine local faire. This one is extra special because it doesn’t take place at one location, rather a series of venues along the Hudson Valley Rail Trail, including the Uster Welcome Center Plaza.

This is another farmer’s market-type event, taking place in early October, but indicative of the variety of these sorts of events throughout Ulster County.

Woodstock-New Paltz Arts & Craft Fair

The Woodstock-New Paltz Fair is an ever-popular event for Ulster County locals and visitors alike. Located at the Ulster County Fairgrounds, this event includes displays and stalls from a variety of artisans, artists, and craftspeople, as well as food stalls, activities, and events. 

Ulster County is a charming and naturally beautiful area and every fall it hosts a wide range of events to enjoy. In addition to the cultural and commercial events, like the many fairs and farmer’s markets, there are also the wild natural spaces to enjoy. Some of the largest of these include Wilderness areas like the Sundown Wild Forest, Slide Mountain Wilderness, Big Indian Wilderness, Balsam Lake Mountain Wild Forest, Vernooy Kill State Forest, Awosting Reserve, and Bluestone Wild Forest.

So if you’re looking for something to do this fall in Ulster County, consider taking a hike along one of the many trails in these parks to enjoy the fresh air and fall colors! 

Posted by Dylan Taft on
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