Top 10 Events in October

Date Published: September 24, 2020

Our monthly list of Top 10 Events has been altered to ensure everyone can experience Dutchess’ exciting happenings – both virtual and in-person (while maintaining social distancing to keep everyone safe)!

1. Woodstock Film Festival at Overlook Drive-In 

Thursday, October 1 through Sunday, October 4th at 7:00 p.m. at Overlook Drive-In Theater 

Even though the Woodstock Film Festival looks a bit different this year, you can still watch their selected indie films at Overlook Drive-In! Visit early and enjoy dinner from Overlook's full-service concession stand. Join the conversation with a live Q&A preceding the screening. You can also join this year’s festival virtually with a film festival pass option, allowing you full access to the overall online programming, or purchase an individual ticket to any of the films for online viewing. Whether it's on the giant drive-in screen or at your fingertips and on your computer, enjoy this year's diverse selection of features, shorts, panels, and special events! For tickets and more information click here. 

2. Lucky Hops Presents Oktoberfest Bier Experience 

Saturday, October 3 with sessions at 12:00 p.m., 1:00 p.m. and 4:00 p.m. at Revel 32

Join fellow beer lovers at Lucky Hops’ Oktoberfest Bier Experience at Revel 32, featuring King’s Court Brewing Company and Mill House Brewing Company from Poughkeepsie and Torch & Crown Brewing Company from Manhattan. Your half-full pitcher is refillable for the entirety of your session, and feel free to have open discussions with brewers! Enjoy beer-themed trivia, pretzels, and brats with homemade sauerkraut. For more information, click here. 

3. 8th Annual Old-Fashioned Cider Tasting by Cider Mill Friends 

Saturday, October 3 from 11:00 a.m. to 4:00 p.m. at Kimlin Cider Mill 

Have an old-fashioned cider tasting at Kimlin Cider Mill! Enjoy sweet ciders available in pre-packaged, to-go sample packs, plus a cider pressing demonstration using an antique cider press. Along with tasting freshy-made Kimlin Cider, this event showcases an assortment of samplings from other Hudson Valley cideries behind-the-scenes tours of the mill, and an online auction. Visitors are required to purchase their tickets ahead of time, as only 50 attendees will be permitted at once. Enjoy made-to-order apple fritters by the Fishkill Historical Society and learn about the work this group does to preserve local history. The Sports Museum of Dutchess County will also exhibit at the event. All proceeds benefit the restoration of the Kimlin Cider Mill. For more information click here. 

4. Mid-Hudson Children’s Museum Presents Outdoor Program: Saturday Storytime!

Saturday, October 3 from 10:00 a.m. to 11:00 p.m., and 1:00 p.m. to 2:00 p.m. at Mid-Hudson Children’s Museum 

Get creative with silly stories, songs, and a messy art project or two in the Outdoor Program: Saturday Storytime! Open to children between the ages of three and four, this outdoor program will be held in the open-air waterfront pavilion and limited to 20 participants. Registration is required. Each participant group will be assigned to a separate workstation to ensure appropriate social distancing. Materials will not be shared and face masks are also required. For more information, click here. 

5. Hudson River Cruises Fall Foliage Boat Tour from Poughkeepsie 

Saturday, October 3 and 17 at 11:15 a.m. at Waryas Park in Poughkeepsie 

Book a Fall Foliage Boat Tour by Hudson River Cruises with a special departure from Waryas Park in Poughkeepsie. Hop aboard the Rip Van Winkle II for a fantastic two-hour sightseeing cruise and enjoy captivating stories and historical narration aboard the three-deck vessel. On this river adventure, you’ll enjoy the gorgeous fall landscape the Hudson Valley is known for, and get a clear view of historic Hudson River lighthouses waterfront mansions, and other notable locations. Take the Metro-North Hudson Line to Poughkeepsie Station and use promo code MNR when booking for an exclusive $5 off adult and $2 child tickets. Book your tour online here. 

6. 2020 Virtual Sheep and Wool Festival 

Thursday, October 15 through Sunday, October 18 from 9:00 a.m. to 4:00 p.m. 

Although normally an in-person event, this year you can attend the 2020 Virtual Sheep and Wool Festival from home! This year’s show  features over 100 workshops, kids activities, breed talks, demos, a fleece-to-shawl competition, the ‘NY Make it with Wool’ event, and the annual photo and art contests. Visitors can also look forward to shopping with all of the 2020 vendors as well as the fleece sale in the virtual marketplace. All events will be held online. For more information click here. 

7.ArtEast Open Studio

Saturday, October 17, 18, 24, and 25 from 11:00 a.m. to 5:00 p.m. at various locations throughout Dutchess County 

Join ArtEast Open Studio virtually or in-person and support local artists! Here’s your chance to meet working artists, ask questions about their process, and view their artwork. A guided, virtual 3D ArtEast Gallery Tour is also available to view here. Even though there will be fewer studios open for in-person tours, you can still enjoy a drive through scenic Dutchess towns like Dover Plains, Amenia, Wingdale, Poughquag, Hopewell Junction, Holmes, Patterson, and Pawling. Please visit arteastdutchess.com to see which artists are opening their studios to the public. Can’t get enough? Also happening virtually this year is the Hudson Valley’s premier juried art show, Fall for Art. Join this reimagined event with new expanded exhibition dates Sunday, October 25 through Wednesday, October 30. For more information click here.

8. Kevin McCurdy’s Haunted Mansion Presents ‘The Wicked Woods’

Weekends in October, plus Thursday, October 1 and 29 at 7:30 p.m. at Kevin McCurdy’s Haunted Mansion

Are you ready for the walk of your life? Prepared to be scared at Kevin’s McCurdy’s Haunted Mansion’s new, all-outdoor experience: The Wicked Woods! Presenting their 44th season, this year’s spine-chilling tour will be held on their newly-expanded outdoor trail. Get ready to experience one mile of chills and thrills with life-size, western ghost towns, and dinosaurs! Tickets must be reserved in advance. For more information, click here. Looking for a spooky overnight? Book the Dungeon Room at Wing’s Castle in Millbrook.

9. The Center for Performing Arts Presents Double Dare Drive-in: Back-to-Back Classics

Every Friday and Saturday in October  from 7:00 p.m. - 10:00 p.m. at The CENTER for Performing Arts at Rhinebeck  

Watch a double feature of classic, black and white, Universal horror films on a huge 40-foot screen from the great lawn of The CENTER for Performing Arts! Spooky films will be playing on Fridays and Saturdays in October with showtimes at 7:00 and 8:30 p.m. Bring your whole family and enjoy classic films like “Dracula,” “The Wolfman,” “Frankenstein” and more! The concession stands will be open; masks are required when leaving your vehicle. All tickets must be purchased in advance, click here for more details. For more chilling titles visit Four Brothers Drive-In Theater playing thrillers throughout October. Check Overlook and Story Screen Drive-In schedules soon for possible spooky flicks.