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The October Events You Need to Check out in the Hudson Valley

There are so many exciting October events. Adobe Stock / EvgeniiAnd

October means fall is in full swing in the Hudson Valley, so check out these exciting events to look forward to this month.

The Olana Plein Air Festival Olana State Historic Site, Hudson

October 1, 7 a.m.–7 p.m.

Here’s your opportunity to follow in the footsteps of Hudson River School painters. Whether you’re a beginner or expert, bring your supplies and paint your own landscape throughout Olana’s 250 acres. olana.org

Frost Valley Dinner — Claryville

October 1

Join a group of perfect strangers for a communal meal of local wines and a multi-course dinner. Presented by Terrain & Table of The Farmhouse Project, the dinner will be prepared by guest chef Linda Laestadius of Kingston’s Grounded. Come early to explore the grounds of Frost Valley YMCA and mingle with other attendees. thefarmhouseproject.com

Handcrafted Octoberfest at Rhinebeck — Dutchess County Fairgrounds

October 1–2, 10 a.m.–6 p.m.; Sunday until 5 p.m.

Celebrate fall and spend a day at this festival packed with handcrafted and artisanal goods, and agricultural vendors. There’s also some great food and wine, beer, and spirits. dutchessfair.com

loop trail scare tactics

By Greg Miller

Did you know?

The Hubbard Perkins Loop—a scenic, 9.5-mile-long-trail in the northern end of Fahnestock State Park—reopened this summer. The revamp took two years and $1.5 million to complete, with help from the Open Space Institute, a conservation organization, and cadets from the United States Military Academy at West Point.

Hudson Valley Garlic Festival — Saugerties

October 1–2

Celebrating the annual harvest of the “stinking rose,” this festival showcases all things garlic, including farmers and goods at Cantine Field. While you’re there, you can also enjoy live music, children’s activities, and a selection of locally made arts and crafts. hvgf.org

Warwick Applefest — Warwick

October 2

Returning to the Village of Warwick following a two-year hiatus, this highly anticipated, one-day event fills the streets with over 200 craft and food vendors, apple farmers, musical entertainment, and a kid’s carnival. Storefronts will also be open for perusal by Applefest’s nearly 30,000 visitors. warwickapplefest.com

legoland halloween october events

Photo courtesy of Legoland NY

legoland fall october events

Looking for October events for the kids? Head to LEGOLAND! Photo courtesy of Legoland NY

Brick-or-Treat Presents Monster Party — Goshen

Weekends throughout October

A special event for the spooky season, monsters take over LEGOLAND to celebrate Halloween! Go trick-or-treating throughout the park, participate in costume contests, view holiday-specific shows, and more—all included in a regular day pass to the park. legoland.com

Field + Supply Fall MRKT — Kingston

October 7–9

Taking over Kingston’s Hutton Brickyards for its last 2022 festival, the fan-favorite Field + Supply MRKT once again brings some of the best local art and crafts, homewares, and food and drink vendors to the west bank of the Hudson. Enjoy riverside eats and live entertainment while you shop! fieldandsupply.com

O+ Festival — Kingston

October 7–9

An annual celebration of art, music, literature, and wellness, O+ will be in Kingston for the second weekend in October with performances for all to enjoy! Free to the community, this festival offers artists healthcare clinics in exchange for performances. Donations encouraged. opositivefestival.org

In the Landscape: Osios–Sculpted Views of the Hudson River Valley — Garrison

October 9, 10 a.m.

In the Algonquin language, Osio means “beautiful view;” there are four throughout Manitoga’s woodland trails created by Russel Wright that frame the Hudson. Embark on this 1.5-mile hike to view them all! visitmanitoga.org

spirited away

Courtesy of CBS Entertainment

If you’ve ever wondered what it would be like to live in a haunted Hudson Valley home, tune into the comedy “Ghosts.” Married couple Samantha and Jay—a freelance journalist and chef, respectively—inherit a large, run-down Ulster County estate and are determined to turn it into a charming B&B. The only problem is that there’s a close-knit group of deceased residents—including a 1700s militiaman and a hippie from the ‘60s—who are not too happy about the renovation. Season two of the show, which is based on a British series of the same name, will air in late September—you can catch up on the first season on Paramount Plus. – Megan Ashcroft

Related: This Historic (and Possibly Haunted) Hudson Valley Home Is for Sale

Peace, Love and Pumpkins — Bethel

October 14–30, 6:30–10 p.m.

Open nightly, this family-friendly Halloween walk-through returns to the historic grounds of Bethel Woods for its second year. Experience intricate and hand-carved jack-o-lanterns at every turn of the venue’s garden trails. Stop by on the 21st or 28th for surprise scares as part of the haunted Friday Night Frights (but leave the kids at home if they’re easily spooked!). bethelwoodscenter.org

sheep and wool festival event october

The Sheep & Wool Festival is a must when it comes to October events. Photo by Benjamin Fractenberg

Sheep & Wool Festival — Rhinebeck

October 15–16

Fiber artists and animal lovers—this one’s for you! It’s a weekend full of fleece and yarn crafts vendors, workshops, a camelid (an animal related to camels) and cashmeres barn, sheep herding demonstrations, and a petting zoo. dutchessfair.com

Fortune Feimster: Hey Y’all — Troy

October 20, 7 p.m.

Down-right funny Feimster cracks jokes about her many experiences as a North Carolinian and member of the LGBTQ+ community. Experience her new hour for the “Hey Y’all” tour at the Troy Savings Bank Music Hall! troymusichall.com

Paula Poundstone — Tarrytown

October 21, 8 p.m.

Known for her clever and observational humor, Poundstone is sure to bring Tarrytown Music Hall down with wit, jokes, and outrageous stories. tarrytownmusichall.org

Pete Seeger stamp

Courtesy of the United States Postal Service

Pete Seeger—beloved folk singer, social activist (and founder of the Sloop Clearwater), and long-time Beacon resident—was recently honored with his very own postage stamp. The USPS expects it to be a huge hit, they printed 22 million!

Fall Festival — Scarsdale

October 22–23, 10 a.m. –3 p.m.

Enjoy the height of the fall season with activities for all ages at the Greenburgh Nature Center. Live music, DIY crafts, games, a pumpkin and scarecrow walk, vendors featuring handmade goods, and apple cider demonstrations and tastings fill out the two-day event. greenburghnaturecenter.com

Art After Dark — Poughkeepsie

October 28, 6–11 p.m.

Come to the Trolley Barn Gallery on Main Street for a variety of food, cocktails with an artistic twist, and of course, art! Immersive experiences created by The Art Effect staff and youth will be the event’s headliner. thearteffect.org

Halloween Haunts & Happenings — New Paltz

October 28–31

From interactive tabletop “whodunnit” games to a haunted tour, tomahawk throwing, movie marathons, and more, experience Mohonk Mountain House and its grounds during this weekend packed with festive, family-friendly activities. mohonk.com

Night of 100 Pumpkins — New Paltz

October 31

Slated to return this Halloween following a pandemic hiatus, this display of carved and painted pumpkins, live music, and free apple cider and pumpkin bread is a staple of New Paltz’s holiday festivities. Just bring your pumpkin to The Bakery on North Front Street on October 30 and fill out an entry form to participate. ilovethebakery.com

Related: 20 Breathtaking Fall Hikes to Take in the Hudson Valley