Things to do

12 Hudson Valley fall outings to put on your 2026 calendar

Plan a fall day or two around live music, food, jack o’lanterns, handmade goods, and the Hudson Valley’s most memorable seasonal traditions.

Photo of sppoky Halloween decoration in Sleepy Hallow New York
Photo source: Maria Florencia Rossi/Shutterstock

Fall in New York comes with plenty of reasons to make weekend plans. Across Rockland, Putnam, northern Westchester, and southern Dutchess counties, the season’s calendar includes outdoor concerts, art events, book fairs, food festivals, and more.

Here are 12 events in New York to put on your calendar this fall, with options for every member of the family to enjoy:

1. Fall Crafts at Lyndhurst

More than 200 makers, artists, and designers take over the grounds of Lyndhurst Mansion for a weekend of handmade shopping from jewelry and fashion, to art, home goods, and early holiday gifts.

When: Sept. 18, 10 a.m.-5 p.m., Sept. 19, 10 a.m.-6 p.m., Sept. 20, 10 a.m.-5 p.m.

Where: 635 South Broadway, Tarrytown

Cost: Online prices are $13 for general admission, $12 for seniors, $6 for children 6-16, while children 6 and under can enter for free. Service fees are included on the event’s website.

2. The Great Jack O’Lantern Blaze

This polished nighttime walk through Van Cortlandt Manor is one of the Hudson Valley’s signature fall outings. More than 7,000 illuminated hand-carved jack o’lanterns light up elaborate scenes and structures, making it a great pick for families, date nights, and anyone planning on a spooky photoshoot.

When: Sept. 18-Nov. 8

Where: Van Cortlandt Manor 525 S Riverside, Croton-on-Hudson

Cost: Timed tickets start at $24 online here. Advance tickets are required and not sold on-site.

3. Oktoberfest with the Amish Outlaws

The Amish Outlaws bring a high-energy singing and dancing show to Mahopac for an outdoor Oktoberfest opener with German-style food such as bangers, knockwurst, kielbasa, and draft beer.

When: Sept. 18, 6:30 p.m.-10 p.m.

Where: 187 Hill Street, Mahopac

Cost: Ticket prices are $37 +tax online and $50 on-site.

4. The Echotones at River Hook Preserve

The Echotones transforms River Hook Preserve into an outdoor music and art trail at this September event. Visitors can follow the EcoTones @ River Hook: Guardians of the Shoreline for ensemble performances, student artwork, and participatory community art-making while taking in the Hudson River setting. It is “BYO-Everything,” so be sure to come with a camp chair, snacks, water, and comfortable walking shoes.

When: Sept. 19, 2 p.m.-4 p.m. (Sept. 20, 2 p.m. if rain)

Where: River Hook Preserve, 626 North Broadway, Nyack

Cost: Online tickets prices range from $13 to $103 for general admission with donations added. Check the website for more.

5. Rhinebeck Porchfest

Rhinebeck Porchfest turns the village into a walkable, one-day concert with local musicians playing on porches, lawns, and sidewalk stages. It is a relaxed, choose-your-own-route afternoon: Wander between sets, stop for lunch or coffee, and take in live music without buying a ticket!

When: Sept. 19, 11 a.m.-6 p.m.

Where: Various locations throughout Rhinebeck Village

Cost: Free!

6. Fall Book Fair for Grown-Ups!

Oblong Books invites readers to Rose Hill Farm for a book-centered happy hour with pop-up stalls, cider from the farm taproom, and food trucks. It is the most bookish entry on this list, and a good excuse to make room in the house for one more title.

When: Sept. 25, 4 p.m.-7 p.m.

Where: 19 Rose Hill, Red Hook

Cost: Tickets go for $11.49, with online fees included, while food and drinks are sold separately.

7. Autumn Art Party (A RoCA Fundraiser)

Rockland Center for the Arts’ Autumn Art party is a gallery night with a festive edge: art viewing, cocktails, and a live performance from founding member of Spyro Gyra and pianist/Grammy nominated composer Jeremy Wall. This fundraiser offers a polished alternative to people seeking an arts-and-culture night out rather than a traditional fall festival.

When: Sept. 26, 6:30 p.m.-9 p.m.

Where: 27 South Greenbush Road, West Nyack

Cost: Gala tickets go for $100 per person, but students, seniors, and members can go for $75.

8. Putnam County Pickle Fest

We’ve got one of the most delightfully strange food events here: Putnam County Pickle Fest features more than 50 vendors serving pickle-themed foods, along with Hudson Valley makers and craft vendors. Pickle ice cream and pickle donuts, anyone?

When: Sept. 26-27, 12 p.m.-7 p.m.

Where: 65 Front Street Patterson

Cost: Tickets begin at $15.11. Be sure to check the website for more information.

9. Putnam Arts Council Art Party Benefit

The Putnam Arts Council Art Party Benefit brings artist displays, interactive workshops, and outdoor entertainment to Mahopac for an evening celebration of local art. It is a more low-key fall option for people who want to support area artists and spend a few hours making or browsing something creative.

When: Oct. 3, 4:30 p.m.-7:30 p.m.

Where: Putnam Arts Council, 521 Kennicut Hill Road, Mahopac

Cost: Tickets depend on memberships and donations so check the Putnam Arts Council website for admissions, donation, or fundraiser ticket details here.

10. Sleepy Hollow Music Festival

A riverside music festival next to the historic Tarrytown Lighthouse is an easy way to celebrate the spooky Halloween season. The event includes live acts, a children’s zone, and newly added Halloween-everything programming such as a costume parade, Halloween crafts, food, treats, and drinks! 

When: Oct. 3, 12 p.m.- 8p.m. (gates open at 11 a.m.)

Where: Kingsland Point Park, Sleepy Hollow

Cost: General admission tickets are available now for $62.50

11. Nyack Famous Street Fair

Downtown Nyack’s fall street fair fills the village with more than 300 exhibitors, food vendors, and handmade goods. It is the last scheduled fair of the year, good for all ages on a Sunday, and a great way to combine browsing with brunch, galleries, or a Hudson River walk.

When: Oct. 11, 10 a.m.-6 p.m.

Where: 9 N. Broadway, Nyack

Cost: Free!

12. The New York State Sheep & Wool Festival

Often referred to simply as “Rhinebeck,” this nationally renowned festival is a must for knitters, fiber artists, and makers. But livestock exhibits, working shepherds, hands-on workshops, craft vendors, demonstrations, and food options make it enjoyable even for attendees who do not know their merino from their mohair.

When: Oct. 17-18, 9 a.m.-4 p.m.

Where: 6550 Spring Brook Ave, Rhinebeck

Cost: Pre-sale tickets are $15 with an additional online convenience fee, or pay $18 at the gate. Children 11 and younger can enter for free.


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  • Jessica F. Simmons is a Reporter & Strategic Communications Producer for COURIER, covering community stories and public policies across the country. Featured in print, broadcast, and radio journalism, her work shows her passion for local storytelling and amplifying issues that matter to communities nationwide.