The holidays are right around the corner once the calendar flips to November, and New York’s Hudson Valley has its own, distinctive charm at this time of year.
There are many exciting experiences waiting for you here in Dutchess County this month! Here is a sampling of what November has to in store for you, 10 can’t-miss events that showcase the best of what Dutchess has to offer (plus one bonus event, of course!).
Keep that camera handy! Share your photos here and tag @DestinationDutchess on social media.
And, don't forget, Hudson Valley Restaurant Week is set for Nov. 2–16, 2026, so bring your appetites!
By appointment, October through January at Hudson Beach Glass, Beacon
It only takes 15 minutes to create a beautifully festive glass holiday ornament of your very own, one which will bring holiday cheer to your home year after year and can be handed down from one generation to the next. It’s a terrific activity to do as a family. Choose from more than two dozen styles. You can either pick up your ornament the following day after it cools or arrange to have your ornament shipped to you. Click here to book your appointment. Located in a re-purposed historic firehouse on Main Street, the Hudson Beach Glass studio is within walking distance of the Beacon Metro-North train station, so getting there is a breeze! Plus, Beacon’s walkable Main Street corridor features a variety of great restaurants and attractions, so make a day of it!
It’s time to start planning those holiday cards, and if you’re looking for a warm and fuzzy photo opportunity, Dutchess County has you covered.
• Clover Brooke Farm (Hyde Park): Clover Brooke hosts a variety of animal experiences, including llama and alpaca hikes. Shop in their store for a variety of yarn products, as well as handcrafted soaps — perfect to give as gifts, or to keep for yourself!
• Lilymoore Farm (Pleasant Valley): Schedule a trek or a tour and meet and greet alpacas, llamas and an assortment of other farm animals. If you’re looking for gift ideas, look no further than Lilymoore’s shop, which is open Thursdays–Mondays from 10 a.m.–3 p.m. and offers a variety of sustainable, eco-friendly alpaca products!
Related: Top 10 Hidden Gem Hikes
Sunday, Nov. 1, 2026, at The Stissing Center for Arts & Culture, Pine Plains
Housed in what was previously Pine Plains' beloved movie house, The Stissing Center honors its cinematic roots with this second annual celebration of short films created by Hudson Valley filmmakers. Each screening features a Q&A with the creator, giving audiences a chance to meet the filmmakers and hear their stories. Click here to purchase tickets.
Saturday, Nov. 7, 2026, 1–5:30 p.m., at the KuBe Art Center, Beacon
Held every other year, the multi-day Beacon Bonfire Music + Arts Festival has grown into an incredibly successful event. In fact, the five-day festival in 2025 featured more than 400 artists and performers at more than 20 venues throughout Beacon — from fire dancers to poets, muralists to musicians. In order to bridge the gap between the 2025 and 2027 festivals, the folks at the Beacon Bonfire have cooked up a one-day "Baby Bonfire," which will feature music, art, food trucks, activities and more. Click here for complete details, and stay tuned for updates on the 2027 extravaganza!
Saturday, Nov. 7, 2026, 1–5 p.m., at Boutique Wines, Spirits & Ciders, Fishkill
Enjoy an amazing afternoon of tasting artisanal and delicious wines, hand-selected for your holiday season! Taste exquisite white, red, rosé, and sparkling wines, and savor the flavors of the season while mingling with fellow wine enthusiasts. More than 50 wines will be open for tasting — along with a few spirits. Click here to learn more.
Sunday, Nov. 8, 2026, 10 a.m.–3 p.m., at the MJN Convention Center, Poughkeepsie
All aboard! The Hudson Valley Railroad Society's annual train show features an enjoyable day of model trains and vendors, fully operating model train layouts, character photo-ops, food and more. Click here to purchase tickets. Proceeds from the hobby show will benefit the 1914 Hyde Park Station Museum. That historic station was slated for demolition in 1975 when the HVRRS stepped in and saved it. In the more than 50 years since, the HVRRS has been restoring the station and preserving the history of the railroads in the Hudson Valley.
• "Come From Away" (Up In One Productions, CENTER for Performing Arts, Rhinebeck, select dates, Oct. 30–Nov. 22, 2026): Using music, humor, and warmth, "Come From Away" tells a true story of empathy, generosity, and shared humanity that came out of the horrors of the terrorist attacks of Sept. 11, 2001.
• "Peter and the Starcatcher" (County Players, Falls Theatre, Wappingers Falls, select dates, Nov. 6–21, 2026): The County Players, one of the longest running community theatre companies in the area, presents this whimsical musical adventure, which is a grown-up prequel to "Peter Pan."
• "The Pirates of Penzance" (Gilbert & Sullivan Players, Bardavon 1869 Opera House, Poughkeepsie, Nov. 21, 2026, 7:30 p.m.): Set sail with this classic Gilbert and Sullivan comedy, which first opened in New York in 1879, has seen more than 40 revivals since then, and boasts one of the most famous patter songs in musical theatre history, the "Major-General's Song."
Friday, Nov. 13, 2026, 7:30 p.m., at the Bardavon 1869 Opera House, Poughkeepsie
Spend an evening with folk music icon Judy Collins, whose luminescent stage presence shines as brightly today as ever. Her amazing career has spanned more than 60 years and includes 55 albums. Her 1967 rendition of Joni Mitchell's "Both Sides Now" earned Collins her first Grammy Award. She also enjoyed much success with her versions of Pete Seeger's "Turn! Turn! Turn!" and Stephen Sondheim's "Send in the Clowns." The namesake of the Crosby, Stills & Nash song "Suite: Judy Blue Eyes," Collins will be bidding adieu to the road after this farewell tour, so don't miss this opportunity to see a true legend in concert. Click here to purchase tickets.
Sunday, Nov. 15, 2026, 2–4 p.m., at Millbrook Vineyards and Winery, Millbrook
Arts Mid-Hudson and Millbrook Vineyards and Winery team up to present this annual project in which artwork is transformed into original labels for wine bottles. At this closing reception, enjoy hors d’oeuvres and desserts and wine from Millbrook Vineyards (of course!) as you mingle with the participating artists, one of whom will be crowned the winner of this year’s competition. Click here to reserve tickets.
Related: The Dutchess Tourism Taste Finder Craft Beverage Trail
Saturday, Nov. 21, 2026, 5 p.m., at the MJN Convention Center, Poughkeepsie
A Guinness World Records record-holder for Most Tickets Sold for a Stand-Up Comedy Tour, ventriloquist and comedian Jeff Dunham has sold millions of tickets worldwide and performed in sold-out arenas across more than 20 countries. For more than three decades, Dunham has captivated audiences around the world with his one-of-a-kind blend of stand-up comedy, unforgettable characters, and razor-sharp wit. Click here to purchase tickets to his show at the Majed J. Nesheiwat Convention Center. If time allows, make a weekend of it! The DoubleTree by Hilton Poughkeepsie is right next to the convention center and is within walking distance of several attractions and restaurants.
Nov. 23 or Nov. 24, 8 a.m.–12 p.m., at The CIA, Hyde Park
Learn to cook like the professionals! Bake delicious pies that steal the show at your family gatherings. Just in time for the holiday season, these one-day classes at the world-renowned CIA will teach you the secrets of dough-mixing, rolling, decorative borders and lattice work. Learn tips and tricks from CIA chef instructors that will take your pie-baking skills to the next level. Click here to register.
