Event & Activities In The Catskills & Hudson Valley | October 2024
Posted by Coldwell Banker Village Green Realty on Thursday, October 3rd, 2024 at 11:17am
The most beautiful season in the Catskills and the mid-Hudson Valley is the autumn – we feel ok about making that pronouncement. The weather is cooling down, but October is inarguably the month with the hottest Upstate NY events! If you want to see the changing colors of the trees, eat some great food, or experience the art and culture of Upstate, we here at Coldwell Banker Village Green Realty, like a comfy cashmere hoodie - have you covered! It’s sweater weather Upstate, here are our picks for the best place to wear your favorite this October 2024.
Windham’s 30th Annual Autumn Affair
Where: Main Street, Windham
More for the leaf peepers! This is one of the most popular events in Windham, so bring your friends, family, or neighbors with you to Main Street! There will be live music from the Tom Pettys and other musical guests alongside more than 50 vendors on Main Street. Coldwell Banker Village Green Realty’s offering is our incredibly popular “Smooch-A-Pooch” Beauty Contest. Bring your pup for a fall-themed portrait by our in-house photographer. We put them on Instagram and Facebook the next week and the voting for the most good-looking dog begins! Prizes are announced at the close of voting. Come, and take in the gorgeous views of the northern Catskills while seeing what Windham has to offer, on and off the mountain.
Catskill Mountain Railroad
Where: Kingston, New York
Catskill Mountain Railroad offers a unique way to see the foliage. The train takes you on an hour plus ride through the scenic Hudson Valley in antique and open train cars. Their Pumpkin Express rides on the 19th, 20th, 26th, and 27th are a one-of-a-kind trip to a pumpkin patch to pick a pumpkin out for carving when you return home.
Headless Horseman Hayride and Attractions
Where: Ulster Park, NY
This is the time of year when the veil between the living and the dead is thinnest (muhahahahaha!). If you love horror, look no further than the #1 rated haunted house and live horror experience in America, The Headless Horseman Hayride!!! The Headless Horseman has multiple haunted houses: a broken-down hotel, a diner/slaughterhouse, a creepy motel, plus several corn mazes. It’s fun for most everyone (you scaredy cats need not apply), so bundle up and show up for an unforgettable experience... IF YOU DARE!!! Note: Most days, children under 8 are not admitted & children 15 years old and younger must be accompanied by an adult 21 years or older – this is genuinely scary stuff!
ChipandGus
Where: Bridge Street Theatre, Catskill
A modern day “Waiting For Godot”, “Chip and Gus” follows two lonely guys who hang out once a month in the back room of a Schenectady sports bar. Ping Pong paddles feature prominently in this purportedly hilarious comedy.
Hudson Jazz Festival
Where: Hudson, New York
The small city of Hudson in Columbia County has a very high cool quotient on any given weekend. But the first weekend in October it is playing host to performance after performance by Jazz luminaries like Ekep Nkwelle, The Riley Mulherkar Quartet, and The Ethan Iverson Trio. Attend the mainstage shows and wander through town for pop-up performances, antique and art shopping, and dining.
Friday, October 11th Through Sunday, October 13th
Always Patsy Cline
Where: Phoenicia Playhouse, Phoenicia, New York
A musical comedy about a pen-pal friendship set to the music of Patsy Cline. Presented with a live Honky Tonk band, the hills of Phoenicia are alive with classic country thanks to this small-cast musical – don’t miss it!
Half Waif Album Release Show with Elori Saxl
Where: Chatham, New York
PS21: The Center For Contemporary Performance in Chatham has been lauded by The New York Times as a vibrant organization that, “presents work that challenges and invites.” October 5th they’re presenting, “Chatham-based singer, songwriter, and producer Nandi Rose, who records and performs internationally as Half Waif, premieres the songs from her new record, See You At The Maypole… Rose leads an eight-piece ensemble through this complex work, which grows out of her classical piano training towards pop songwriting styles with experimental electronic production and expansive arrangements.” If you don’t already frequent PS21 this is an opportunity to support a nationally recognized local artist.
Handcrafted Octoberfest at Rhinebeck
Where: Dutchess County Fair Grounds, Rhinebeck, New York
What would October be without an Octoberfest? BUT, sometimes an Octoberfest can be a little one-note. If you don’t loooooove beer, at many Octoberfest celebrations the best entertainment you can expect is to admire the art on the beer cans. This one’s different. The Handcrafted Octoberfest has beer, but it also has art and beautiful hand-made goods by Hudson Valley artisans, music, and it has activities for kids. There are giant pumpkins and juried art exhibitions. If you need an eight-note Octoberfest, this one’s for you! Prost!
Harvest Hoedown
Where: Rondout Valley Growers Association, Stone Ridge
This is the 17th year the Rondout Valley Growers Association has hosted this hoedown. Come! Dance! They know how to throw a real harvest celebration.
Saturday, October 12th & Sunday, October 13th
Fall Festival Belleayre
Where: Belleayre Mountain, Highmount, New York
Here is another opportunity for food, beer, and fabulous scenery in a mountain town – this time in Highmount. Belleayre Mountain’s offerings include a cornhole tournament (yes!), hatchet throwing (even better!), a pie eating contest (sign us up), or disc golfing (skeptic? read our disc golfing guide). Those that go primarily for the views can take a gondola ride to the top of the mountain and back!
Hike: 1925 Teenage girls working at the Mountain House
Where: Haines Falls, New York
This hike follows paths trod by the teenage girls who worked at the Catskill Mountain House in 1925 and explored their experience there through pictorial evidence. The hike is led by Chief Archivist Bob Gildersleeve of The Mountain Top Historical Society of Greene County. History buffs, strap on your hiking boots!
"In and Out of Lineage: Tracing Artistic Heritage Through SUNY New Paltz Faculty"
Where: Samuel Dorsky Museum of Art at SUNY New Paltz, New Paltz, New York
Works from 20 SUNY professors explore the dynamic interplay between teaching and creating. “Those who can’t teach, do.” does not apply here. If you’re apple picking in the New Paltz area, this is a quick stop to make for art that will fuel your conversation as you continue to explore.
O+ Music, Art, and Wellness Festival
Where: Uptown Kingston, New York
The O+ festival is wonderful in every sense of the word. This festival showcases of the art, music, and culture of the Catskills in venues all over Kingston, NY. But that’s not all it is. Many artists are underinsured; O+ lets artists trade their art for healthcare services of all kinds from dental work to sound healing. All of Kingston feels alive during O+; the streets are filled with artists, audience members, and health care professionals attending over 55 live music performances, dozens of visual and performance art activations, spoken word pieces, and a BlO+ck Party filled with vendors and a variety of health and wellness workshops open to the public. This is a beautiful time of the year in Kingston made even more beautiful by the foundational spirit that pervades this festival.
Field + Supply
Where: Hutton Brick Yards, Kingston, New York
We can’t believe that this is Field + Supply’s 10th anniversary! This is the maker’s market to shame all others. It’s important to understand that you need to set aside an entire day to see all the beautiful handmade housewares, furniture, clothing, and accessories being offered by artisans both local and global.
Italian American Festival
Where: Kingston, NY
Come one, come all! Tutto Italiano (everyone’s Italian) here! Head to the Kingston Waterfront for a day of Opera, song, dance, culture, and the best Italian food north of Arthur Ave. There’s a spaghetti eating contest, fantastic sausage and peppers, and a lot of other Italian fare. Everything here is fantastic!!! If you are wondering about the authenticity of the event, fuggedaboudit!!! The event organized by the Ulster County Italian American Foundation. Piacere!
Woodstock Film Festival
Where: Woodstock, New York
Going on its 25th anniversary, the Woodstock Film Festival is world-renowned. With venues in Woodstock, Rosendale, Kingston, and Saugerties the festival lets ticket holders enjoy film, music, lectures, and thought-provoking Q&A during peak leaf season in the Catskills. It’s a practically perfect way to spend an extended weekend. This year’s centerpiece film is Blitz directed by Oscar®-winning director Steve McQueen and starring Saoirse Ronan. The closing night film is A Real Pain directed by Oscar®-nominee Jesse Eisenberg. In between are dozens of other films ranging from documentary to family-friendly animation. Rub shoulders with film luminaries and spend some leisure time at the movies.
Haunted History Tour
Where: Warwick, NY
Ready to have your spine chilled? Warwick Historical Society will present its Second Annual Haunted History Tours this October. The one-mile tours are from 5:30 pm - 8:30 pm starting at the AW Buckbee Events Center. Tickets can include the tour and snacks, or the tour, snacks, and adult drinks.
Farm to Yarn Festival
Where: Kingston, NY
This newer, smaller fiber festival is worth checking out if you’re on the west side of the river the same weekend as the NY Sheep and Wool Festival. Hutton Brickyards in Kingston is a river-front venue with fabulous Upstate history and character that will be hosting 100 different vendors, food purveyors, live music, and more - all for the love of wool.
Opus 40 Fall Foliage Gala
Where: Saugerties, NY
Opus 40’s annual gala is a fete like no other. It begins with cocktails and a seated dinner in view of the famous sculpture. There is music and a light show (light shows in themselves are cool – a light show built around Opus 40? Crazy cool!) There’s a bonfire and the s’mores to go with it. Come and bask in the fall at Harvey Fite’s epic creation.
NY State Sheep and Wool Festival
Where: Dutchess County Fair Grounds, Rhinebeck, NY
The Sheep and Wool Festival is a celebration of fiber! There are fiber crafts, fiber demonstrations, fiber workshops, a fiber sale, sheep, alpaca, goats, and bunnies all sporting their fibers – if it has to do with fiber, it will be represented at the Sheep and Wool Festival. If you’ve never been before, we highly recommend this event. There is a 6 page event schedule of workshops and demonstrations and there will be barn after barn of unique fiber crafts, roving and yarn to browse. There’s food there too, of course!
Rosendale International Pickle Festival
Where: Ulster County Fairgrounds
What exactly is a pickle triathlon? Well, it includes a pickle toss, a pickle juice-drinking contest, and a pickle eating contest. This is just one of the vinegar-fueled events at the Rosendale International Pickle Festival! A year or so ago the Pickle Festival outgrew Rosendale– it’s now held at the Ulster County Fair Grounds in New Paltz. The larger festival now hosts over 100 pickle vendors and musical guests Lara Hope and the Gold Hope duo, the Rosendale Improvement Association Brass Band and Social Club, and the Rosendale Ukelele Group!
Hudson Valley Pottery Tour
Where: Shokan, NY
An intimate tour of some of the Catskills best ceramic artist’s studios. Admission is free, just follow the map on their site as you drive the country roads of Ulster County.
Leaf Peeping in the Catskills and Mid-Hudson Valley
Where: Ulster, Greene, and Dutchess County
People come from all around world to witness the natural spectacle that is the fall in our region. Honestly, this is why October is such an events-packed month! While many visitors are content to drive around the country roads looking at colorful scenery all day, some others prefer to see a little less of the countryside in favor of an activity that’s accompanied by pretty leaves. For the first set, here’s some info:
For the second set: See the rest of this article. On your way to and from any of these events you’re going to get a color show.
Mykingstonkids Halloween Fest & Parade
Where: Broadway in Kingston to the Kingston Plaza
3...2...1 Liftoff!!! Get ready for some cosmic, interstellar, and extraterrestrial beings to descend upon Kingston Plaza in a space-themed children’s parade that blasts off at 2pm and ends at the Kingston YMCA parking lot at 3pm where the festivities continue until 7pm. There will be a costume contest held for the best space-themed costume and other activities to delight the whole family - from infinity and beyond!
Still Standing Historical Structures Tour
Where: Kingston, New York
What is now Kingston, New York (formerly known as Esopus) was founded in 1652. The Friends of Historic Kingston offer tours of 12 historic structures in the Uptown district on Fridays and Saturdays from 11:00 AM until 4:00 PM. We’re real estate agents. We don’t think we need to wax poetic about the beauty of historic architecture – it’s kind of where we live. We wholeheartedly recommend this tour! There couldn’t be a better time of year to wander Uptown looking at pretty buildings and imagining earlier times!
Walktoberfest Farmer and Makers Market
Where: Poughkeepsie, New York
The Walkway Over the Hudson is part of the network of decommissioned railroads across New York State that have been turned into biking/walking trails. This trestle bridge has one of the most impressive views of the Hudson River. Walktoberfest, “brings a curated selection of more than 190 of the Hudson Valley’s finest producers – farms, distilleries, breweries, wineries, restaurants, artists, artisans, and more – to the Hudson Valley Rail Trail and west approach to the beautiful Walkway Over the Hudson State Historic Park.” Walk, eat, sip, and repeat amidst stunning fall scenery!
DuBois Farms and Tavern
Where: Highland, New York
Would the farmers of the Hudson Valley from centuries ago chuckle if they knew that spending a day on a farm in the fall has become a luxury this century? Perhaps. But, the truth is, a day on the farm just feels right in the fall. Dubois farm is a beautiful farm where you can pick apples, grapes, and pumpkins. They have a farm stand, pizza, a bakery, a corn maze, live music, and pony rides. Check, check, check! Dress code? Plaid, all the way. Bonus: the weekend of the 26th and 27th is “Classics On The Farm” – classic cars and apple picking? Weekend perfection!
Ashokan Rail Trail
Where: Boiceville, Shokan, and Woodstock New York off Route 28
The Ashokan rail trail is an 11.5-mile trail that runs on the northern side of the Ashokan Reservoir. This flat trail is exquisitely beautiful in the fall - a great way to get 10,000 steps in. The ART, as it’s been come to be known as, is environmentally protected and is loved by everyone who gets the chance to go there. Hiking, walking dogs on leash, bicycling, running, nature observation, cross-country skiing, and snowshoeing are allowed but no use of motor vehicles is permitted on the trail. With 3 trailheads and almost 12 miles to trek, this is a must for the outdoorsy, leaf peepers, and anyone else who loves the aesthetics of fall.
Peekamoose’s Epic Halloween Bash
Where: Peekamoose Restaurant and Tap Room, Big Indian
Dancing, fabulous costumes, and treats from the best kitchen in the Catskills this annual event is a place where Halloween creativity gets a little wild.
Woodstock’s Halloween Parade
Where: Tinker Street, Woodstock
We’re a little biased, having watched over three decades of Woodstock Halloween Parades, but we think this is the best Halloween Parade in all the land. Join the people of Woodstock, known for their creativity, for a show of the most creative costumes you’ll find. The parade starts at 5 – stop by our office for some treats!
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