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An Insider’s Guide to October Events in the Hudson Valley

Tilly Foster Farm / Photo courtesy of Putnam County Tourism

Hudson River tourism directors share their top picks for places to go, sights to see, and things to do throughout October.

We’ve said it before and we’ll say it again. There are a ton of things to do in the Hudson Valley each month. Even in the face of the coronavirus, there exist dozens upon dozens of ways to experience the best of what the region has to offer. While they might not be traditional per se (virtual studio tours, anyone?), they are engaging, entertaining, and 100-percent #flattenthecurve-approved.

To help scout out the best events in the Valley, we reached out to local tourism directors from Albany to Westchester for their top picks for things to do. Check out their selections, then get planning!

Albany County

Discover Albany President and CEO Jill Delaney shares her top recommendations for the month.

Hollowed Harvest

Altamont Fairgrounds, Altamont

We blinked, and Halloween festivities arrived in the Hudson Valley. In the Capital District, Hollowed Harvest leans into spooktacular celebrations with more than 7,000 jack o’ lanterns shaped into stunning landscapes, dinosaurs, zombies, castles, and more. Tickets must be purchased online in advance to attend.

Sightseeing Cruise

Dutch Apple Cruises, Albany
Saturdays and Sundays in October

If you haven’t taken a ride on a Dutch Apple Cruise, October is the perfect month to do just that. Take in the sight of the Hudson Valley in all its autumnal glory during a cruise narrated by a Hudson River historian. Along with leaf peeping, participants can learn more about the landmarks that dot the region’s landscape.

Photo courtesy Discover Albany

Autumn in the Arboretum

The Pine Hollow Arboretum, Slingerlands
October 17, 10 a.m. – 2 p.m.

It’s a big month for The Pine Hollow Arboretum. This October, the Capital Region escape becomes an official protected green space by the Town of Bethlehem. To celebrate, the venue opens its grounds for pumpkin painting, nature crafts, a story walk, and more. Register in advance to attend.

Photo courtesy Discover Albany

Fall Finds Family Scavenger Hunt

Ten Broeck Mansion, Albany
October 24, 10-10:30 a.m.

Kids will love the chance to wander the gardens at Ten Broeck Mansion in search of hidden natural treasures and a few critter friends. Preregistration is required, and groups range from ages 3-7 to 8-14. At the end of the hunt, prizes will be awarded to promote further explorations at home.

Columbia County

Read up on Columbia County Tourism’s highlights for things to do in the Hudson Valley this month.

Photo courtesy Columbia County Tourism

Hudson-Athens Lighthouse Tours

Henry Hudson Riverfront Park, Hudson
October 10, 11 a.m. – 2 p.m.

Is a trip to one of the Hudson Valley’s lighthouses on your local bucket list? Check it off this month during a visit to the Hudson-Athens Lighthouse. After a short boat ride to the lighthouse, attendees can walk through the Hudson River beacon while learning more about the life of a lighthouse keeper. Tours leave on the hour, and advance ticket purchase is recommended.

Photo courtesy Columbia County Tourism

Farm-to-Table Dumpling Sundays

Cooper’s Daughter Spirits at Olde York Farm, Claverack
October 11 and 25, 2-7 p.m.

Cooper’s Daughter proves that dumplings and drinks are the perfect pairing during its two October fests. Mei’s Farm-to-Table Dumplings brings the food, while the distillery dishes up cocktails and drinks. Vegan options are available as well.

Dutchess County

Take a peek at Dutchess Tourism, Inc.’s top picks for things to do in Dutchess County this month.

The Wicked Woods

Kevin McCurdy’s Haunted Mansion, Wappingers Falls
Weekends in October, 7:30 p.m.

Do you dare adventure your way through The Wicked Woods? New for this year, Kevin McCurdy’s Haunted Mansion debuts its terrifying outdoor experience in its 44th season. Get ready for one mile of spooky surprises in a socially distant setting. Masks are required, and reservations must be made in advance.

Photo courtesy of Dutchess Tourism, Inc.

Oktoberfest Bier Experience

Revel 32, Poughkeepsie
October 3 at 12, 1, and 4 p.m.

Poughkeepsie’s renovated event space brings the Oktoberfest experience to Queen City during its three tasting sessions. Ticketed attendees can sample brews from local breweries and enjoy a pitcher for sipping during their session. Along with the beer, the brewers themselves will be onsite to talk about the drinks and the process. As for food, it’s all about pretzels, brats, and sauerkraut…because it is Oktoberfest, after all. 

Photo courtesy of Dutchess Tourism, Inc.

ArtEast Open Studio

Throughout Dutchess County
October 17-18 and 24-25, 11 a.m. – 5 p.m.

Art colors the entirety of Dutchess County during ArtEast’s Open Studio Tour. With both virtual and in-person offerings, the event invites Hudson Valleyites to meet local artists and learn about their methods. For those who prefer to keep close to home, the 3D virtual tour is the perfect way to explore the creativity of the region.

Greene County

Look no further for the coolest attractions and activities in Greene County during the month.

28th Annual Harvest Festival

Angelo Canna Park, Cairo
October 10, 11 a.m. – 8 p.m.

Angelo Canna Park is the place to be for harvest fun in the Hudson Valley. Round up the family for a full day of entertainment beginning at 11 a.m. Admission is free, so stop by for a K-9 demonstration, corn hole contest, pumpkin painting, Disney movie screening, and even an Elvis impersonator. Stick around at night, since fireworks light up the sky at 8 p.m. 

Virtual Hudson Valley Dance Festival

October 10, 7 p.m.

Hudson Valley Dance Festival goes virtual this October to showcase the impressive choreography and performances by a talented cast of dancers. The show streams for an hour, so tune in for everything from modern tap dance to an artistic response to the COVID-19 pandemic.

Living History Event

Crystal Brook-Mountain Brauhaus Resort, Round Top
October 24

History comes alive during Mountain Brauhaus’s reenactment event. In addition to tactical displays, the fest will also feature historical equipment showings, vendors, and food. The resort offers live music from 2-5 p.m. as well.

NYTBF Bassin’ Lane Open

Dutchman’s Landing Park, Catskill
October 25, beginning at sunrise

Fishing begins early on October 25 as part of New York The Bass Federation’s Bassin’ Lane Open in Catskill. After a full day of fishing, the weigh-in goes down at 3 p.m. After that, the fish get released back into the river from which they came.

Orange County

Check out Orange County Tourism Director Amanda Dana’s selections for the best things to do this month.

Hocus Pocus Movie Night

Anthony’s Pier 9, New Windsor
October 2, 7 p.m.

Anthony’s Pier 9 knows that no movie holds October icon status quite like Hocus Pocus. That’s why it invites Hudson Valleyites to its drive-in movie night in New Windsor. Come for the movie, then stay for the cash bar and culinary concessions. Tickets run $50 per vehicle, with a prize awarded for the best car decorations.

Hudson Valley Empanada Festival

Orange County Farmers Museum, Montgomery
October 10, 1-5 p.m.

No, you’re not dreaming. There really is a whole festival dedicated to the empanadas of the Hudson Valley. Head to Montgomery for perfect dough pockets filled with chicken, pork, steak, seafood, and vegan options galore. The region’s top Latin food trucks and restaurants will be onsite, so get tickets before they sell out.

Hudson Valley Plein Air Festival

Wallkill River School of Art, Montgomery
October 13-18, 5 p.m.

Now in its fifth year, the Hudson Valley Plein Air Festival celebrates the beauty and artistry of the region. Across the Valley, local artists unite to paint outside, with works set for public exhibition at the Wallkill River School and online through December.

Hudson Valley Drive-Thru Taco Truck Takedown 4

Thomas Bull Memorial Park, Montgomery
October 17, 1-5 p.m.

One week after its empanada fest, Montgomery keeps the deliciousness coming with its taco truck takedown. The socially distant event takes place in a drive-thru format, with local taco trucks and restaurants onsite for the day. To end the foodie fest on a sweet note, don’t forget to pick up an order of cinnamon sugar-crusted churros for the road.

Halloween Horrorthon

Fair Oaks Drive-In, Middletown
October 31, 6-11:30 p.m.

Only the hardiest of horror film lovers can make it all the way through Fair Oaks Drive-In’s Halloween-themed movie night. The lineup is a good one, with back-to-back Halloween flicks, along with music by Alan Howarth. Tickets run $50 per carload (max four people per car) and $15 for each additional person.

Putnam County

Read up on Putnam County Tourism Director Tracey L. Walsh’s picks for things to do this month.

American Family at Collaborative Concepts / Photo courtesy of Putnam County Tourism

Collaborative Concepts Outdoor Art

Tilly Foster Farm, Brewster
Through October 31

Collaborative Concepts relocates to Tilly Foster Farm for its 15th annual sculpture show this year. Spread across 199 rolling acres, the large-scale show is a delight for sculpture fans who want to get out and stretch their legs in the scenic Hudson Valley.

Manitoga / Photo courtesy of Putnam County Tourism

Visit to Manitoga

Manitoga: The Russel Wright Design Center, Garrison

A true hidden gem in the Hudson Valley, Manitoga offers so much to visitors. On top of hiking around the grounds, guests can check out the venue’s iForest Sunset Concert series on October 3, 10, and 12. The September concerts sold out quickly, so book soon if you want to check out the immersive, multi-sensory experience crafted by Pete M. Wyer.

Tilly Foster Farm / Photo courtesy of Putnam County Tourism

Open House on the Farm

Tilly Foster Farm, Brewster
October 17, 11 a.m. – 3 p.m.

Spend the afternoon at Tilly Foster Farm during its family-friendly open house this October. Kids and adults will love saying hello to the sweet animals, munching on donuts and sipping cider, and meandering through the pumpkin patch. Registration is required, and pets are not allowed on the grounds.

Cold Spring / Photo by Doug Cunningham, courtesy of Putnam County Tourism

Stroll Cold Spring’s Main Street

Cold Spring

On a scale of one to 100-percent charming, Cold Spring is pretty high up there. That’s why autumn is the ideal time to take a wander along Main Street. The easy stroll down to the river is filled with detours through picturesque shops and, at the end, a trip to Moo Moo’s for an ice cream treat.

Rockland County

Take a browse through Director of Economic Development and Tourism Jeremy Schulman’s picks the hottest things to do in Rockland County throughout the month.

Photo courtesy of Rockland County Tourism

Apple Picking

Dr. Davies Farm, Congers and The Orchards of Concklin, Pomona
Throughout October

Autumn in the Hudson Valley just wouldn’t be the same without a trip to one of the region’s apple farms. In Rockland County, Dr. Davies Farm in Congers is open for apple picking daily, with reservations suggested. Nearby, The Orchards of Concklin in Pomona hosts apple picking on Sundays through October 25, with fresh pressed cider and donuts available at the market.

Photo courtesy of Rockland County Tourism

Ride ‘Round Rockland

Rockland Lake State Park, Valley Cottage
October 3, 7 a.m.

Bike your way into October with this socially distant ride through Rockland County. With three routes ranging from 40 to 100 miles, the ride is open to groups and soloists alike. There will be a rest area at The Orchards of Concklin in Pomona, and the race will take place rain or shine.

Photo courtesy of Rockland County Tourism

Classic Volkswagen Beetle Fall Foliage Cruise

October 24, 8 a.m.

Retro riders won’t want to miss Rockland County’s ninth VW fall foliage cruise. The drive kicks off at 9 a.m. sharp in Congers before traversing to Cortlandt, Bear Mountain, and ending at Stony Point for lunch.

Ulster County

Read up on Ulster County Tourism’s event highlights for the month.

Woodstock Film Festival

Multiple locations
Through October 4

A favorite fall happening in the Hudson Valley, the Woodstock Film Festival adapts to keep film aficionados happy and safe. Festival tickets range in price so attendees can pick and choose between online screenings, drive-in showings, Q&As with filmmakers, and panels with industry leaders. Head to the website to scout out the full lineup.


Walkway Over the Hudson, Highland and Poughkeepsie
October 3-4, 12-5 p.m.

Festival season is alive in the Hudson Valley thanks to Walkway Over the Hudson’s socially distant Walktoberfest. Over the course of two days, the mid-Valley walkway rounds up some of the region’s top farms, distilleries, wineries, restaurants, and creatives for an outdoor dining and shopping experience. Tickets run $25 for tastings or $10 for non-drinkers.

Old Dutch Church Cemetery Tours

Old Dutch Church, Kingston
October 3, 10, 17, 24 at 7 p.m.

A little spooky and a lot educational, Old Dutch Church’s cemetery tours take visitors back to the early days of the Hudson Valley to explore the chilling history of the region. Tickets cost $10 per person and must be purchased online in advance.

True Love Will Find You in the End

Denizen Theatre, New Paltz
October 8-18

After a six-month hiatus in response to the COVID-19 crisis, the Hudson Valley’s beloved black box theater is back in action with a world premiere play. Crafted by Tony-nominated Broadway playwright Neil LaBute, “True Love Will Find You in the End” delves into marriage, divorce, and love in life. To keep guests safe, only eight seats are open per performance.

Capital to Capital Run

Virtual and throughout the Hudson Valley
October 11-25

Led by the Rotary Club of Kingston, NY, the Capital to Capital 5K is a run and walk that commemorates the burning of Kingston in October 1777. To remember the journey of Kingston residents on their way to shelter in Hurley, the club invites Hudson Valleyites to run or walk the route of those who fled for their lives during the early days of the region.

Westchester County

Discover the hottest happenings according to Westchester County Tourism this month.

This is a view of the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson on October 12, 2015. (Photo by Tom Nycz) / Courtesy of Historic Hudson Valley

The Great Jack O’ Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson
Through October

The Blaze is back! The Hudson Valley’s electrifying Halloween event fills the grounds at Van Cortlandt Manor with more than 7,000 illuminated jack o’ lanterns in a variety of haunting shapes and sculptures. To ensure social distancing, advance reservations are required.

Sleepy Hollow Cemetery

Sleepy Hollow

Chills and thrills run rampant in Westchester County during the Halloween season, and nowhere is this more apparent than at Sleepy Hollow Cemetery. Visit the hallowed grounds to reminisce upon Washington Irving’s tale of the same name and spot the grave of the author himself, along with the headstones for Andrew Carnegie, William Rockefeller, and members of the Hamilton family.

Leaf Peeping

Throughout Westchester County

With leaf peeping in full force in the Hudson Valley, October is prime time to explore the region in search of those iconic autumnal panoramas. Trek for views at Mianus River Gorge Preserve in Bedford or bring the family to Croton Gorge Park for an easy stroll. Elsewhere, Greenburgh Nature Center, Edith G. Read Wildlife Sanctuary, Rockefeller State Park, and Tarrytown RiverWalk all offer impressive fall foliage displays.

Apple Picking

Harvest Moon Farm and Orchard, North Salem and Wilkens Fruit & Fir Farm, Yorktown Heights
Through October

Don’t let October come to a close without planning a trip to one of the Hudson Valley’s apple farms. In Westchester, Harvest Moon is open for picking by reservation only. Nearby, Wilkens Fruit & Fir Farm operates at half capacity, with a corn maze, bakery, and farm market onsite as well.

Westchester Craft Crawl

Throughout Westchester County
October 24-25

For the first time ever, Westchester Craft Crawl kicks off with more than 30 regional artists in the mix. Locals can look forward to eight studio stops across Cortlandt Manor, Ossining, and Tarrytown, with three to five artists at each location. The event is free to attend, with social distancing guidelines in place and masks required.