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

The Big Sip, an art exhibition, Octoberfest, the New York State Sheep & Wool Festival, and more in October.

Driven to Abstraction: Group Exhibition — North Salem

Through November 12 Featuring the work of nine artists—including Mikel Frank, Rita Maas, and Kurt Steger—this exhibition highlights the unique range of styles that creatives use to convey messages with shapes, colors, forms, and textures. Visitors will gain an understanding of the materials, aesthetics, and processes in abstract art.

“Activate” by Mikel Frank and Gerard Amsellem

Handcrafted Octoberfest — Rhinebeck

October 1, 10 a.m.–5 p.m. Celebrate the season at the Dutchess Fairgrounds for an outdoor maker’s market, craft beer, wine, and spirits, live music, seasonal food, and expert-led harvest activities.

Photo by Tony Scott/ Courtesy of Quail Hollow
horse-drawn carriage
Photo by Tony Scott/ Courtesy of Quail Hollow

Mohawk Hudson Folklife Festival — Albany

October 1, 11 a.m.–5:30 p.m. Join New York Folklore at Albany’s Washington Park for artist demonstrations, live folk music, and cultural cooking lessons. All events will take place at the Lakehouse Amphitheater.

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LEGOLAND Brick-or-Treat — Goshen

October 7–8, 14–15, 21–22, 28–29 On weekends this month, head to LEGOLAND to trick-or-treat throughout the park, see monsters, watch Halloween-themed shows, and more. All events are included in the price of a day pass.

Field + Supply Fall MRKT — Kingston

October 6–8 The biannual maker fair returns to the grounds of Hutton Brickyards with plenty of local crafts, furniture, clothing, jewelry, décor, and more. Plus, enjoy food from vendors like Moonrise Bagels and Oyster Party and listen to live music while you shop.

Cannastock – Milton

October 7, 1–7 p.m. All things cannabis is coming to the Hudson Valley Sportsdome in Milton. Presented by Radio Woodstock, Cannastock will have a “green” market and growers’ showcase, regional food vendors, and live music from SunDub and Andy Frasco & The U.N. Event is for ages 21+.

Courtesy of Radio Woodstock

The Big Sip — Bethel

October 7–8, 1–5:30 p.m. Presented by Bethel Woods, Hudson Valley, and Valley Table, The Big Sip brings the best in regional wine, spirits, and food to the Bethel Woods Center grounds. The weekend will be packed with over 50 alcohol vendors, live music by Andrew McMahon in the Wilderness and Back to the Eighties Show with Jessie’s Girl, a food court, and more. Event is for ages 21+.

Bethel Woods Center for the Arts
Courtesy Bethel Woods Center for the Arts

City That Drinks the Mountain Sky — Saugerties

October 7, 2–3 p.m. Join Arm-of-the-Sea Theater at the Tidewater Center for an educational puppet show on New York City’s water supply, which is based in the Catskills.

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The Grange Fall Fest — Coxsackie

October 7, 4–10 p.m. Head to The Grange, a 90-acre farm estate, for an evening of live music by Cyote Lou and Kegbelly, food and drink, and even tattoos from pre-made designs. Admission is $10.

In Conversation with The Sopranos — Peekskill

October 7, 7:30 p.m. A must-see for fans of the hit HBO show “The Sopranos,” actors Steve Schirripa, Vincent Pastore, and Michael Imperioli take the stage to share memories, stories, and photos from production. Hosted by comedian Joey Kola.

Neil Gaiman: The Bard Lectures — Annandale-on-Hudson

October 12–14 Award-winning author and Bard professor Neil Gaiman will present three lectures on writing and his creative process at the Fisher Center. Signed books will be available for purchase, courtesy of Oblong Books.

The Bard Lectures
Photo by Kyle Bice

“Coraline” — Pleasantville

October 14, 11:30 a.m. Head to the Jacob Burns Film Center for a special screening of the family-friendly fantasy “Coraline.” After watching the stop-motion adaptation of Neil Gaiman’s novel, bring the kids upstairs for an art activity—included in the price of their ticket.

Tri Montgomery Triathlon — Montgomery

October 14, 8:30 a.m. For the second year, join the Business Council of Greater Montgomery for a triathlon event of running, biking, and kayaking. Carb-load the night before at a spaghetti dinner to benefit the local fire department and unwind on Sunday with a yoga class at City Winery.

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New York State Sheep & Wool Festival — Rhinebeck

October 21–22 Calling all fiber arts enthusiasts (and animal lovers): The annual Sheep & Wool festival brings craft vendors, sheep contests, a petting zoo, and crafting workshops to the Dutchess Fairgrounds.

Sheep & Wool festival
Photo by Benjamin Fractenberg

Fall Festival — Schaghticoke

October 27, 10 a.m.–6 p.m. Brave an 11-acre corn maze, pick pumpkins, ride a miniature train, play carnival games, and much more at Liberty Ridge Farm’s family-friendly autumn celebration.

Blippi the Wonderful World Tour — Poughkeepsie

October 27, 6–9 p.m. Known for appearing in educational children’s videos, Blippi and special guest Meekah will take the stage at the MJN Center to perform a brand-new musical. Kids are invited to dance, sing, and learn along.

MyKingstonKids Halloween Fest — Kingston

October 28, 2–8 p.m. This annual Halloween party kicks off at 2 p.m. with a parade that stretches from King’s Plaza to the YMCA on Broadway, where the festivities will continue with plenty of food, games, performances, and more. Don’t forget your Halloween costume!

Breast Cancer
Adobe Stock/ Marigold88

A New Way to Ward off Breast Cancer

October is, as you probably well know, Breast Cancer Awareness Month—an excellent reminder that your best protection is early detection. In addition to yearly mammogram screenings, maintaining a healthy weight, and limiting alcohol, a new study reported in JAMA Oncology reveals that just three to four minutes of vigorous exercise a day can reduce your breast cancer risk. Activities include climbing stairs, strength training, swimming laps, biking (at 14–16 miles per hour), and running. Visit for events all month long, the latest medical news, and more. – Linda Fears

Wildflower Farms
Courtesy Auberge Resorts Collection

Green Getaway

If you’re considering a stay at Wildflower Farms in Gardiner this fall, we highly recommend booking the weekend of October 6–9 when the resort partners with Michelin-starred and plant-based fine dining NYC restaurant Eleven Madison Park. Hotel guests can feast on curated vegan dinners and à la carte specials at the on-site restaurant Clay, take botanical mixology classes, experience cooking demonstrations, and stroll through the beautiful 140-acre property. Visit for more info. – Francesca Furey


Related: Sip Orchard-Fresh Cider at These Hudson Valley Cideries

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