Festivals in Rhinebeck, NY.
Festivals, Craft Shows, Wine-Beer Events

Inaugural Columbia County Craft Festival

October 10 - 11, 2026

hbwinefest.com

(518) 396-9959

Columbia County Fairgrounds - Chatham, NY

Inaugural Columbia County Craft Festival is a country fair featuring crafters, artisans, Farm market and craft beverage tent, children's activities and more!

Handcrafted Octoberfest at Rhinebeck

October 10 - 11, 2026

quailhollow.com

(505) 917-1731

Dutchess County Fairgrounds - Rhinebeck, NY

This festival offers a unique twist on the traditional Oktoberfest celebration, centered around over 100 juried fine art and craft exhibitors. Shoppers also enjoy harvest activities, live music, a master pumpkin carver, an arts and crafts center, a petting zoo, and a giant pumpkin weigh-off.

Eisenhower Park Field 8 Craft & Gift Fair - October

October 10 - 11, 2026

nassaucountycraftshows.com

(516) 442-6000

Eisenhower Park Field 8 - East Meadow, NY

A unique family shopping destination where consumers can interact with and buy directly from the source-Emerging and established local artisans and high quality gift vendors. All vendors offer their handmade and handpicked items at recognizable savings.We are recognized as the #1 producer of Long Island Street Fairs and Nassau County Craft Shows. Free public admission. Enter Eisenhower Park at Field 8 for free parking.

Pearl River Street Festival

October 17, 2026

woodwill.com

(631) 234-4183

105 E Central Ave - Pearl River, NY

Pearl River is nicknamed “The Town of Friendly People” for good reason. The Pearl River Chamber of Commerce began an annual tradition of hosting a community fall festival “Pearl River Day” 16 years ago. It's a day for over 25,000 visitors both young and old to gather in the streets and enjoy over 200 exhibits including live music, great food, Arts, Crafts and many fun attractions.

Suffern Fall Street Festival

October 18, 2026

woodwill.com

(631) 234-4183

Lafayette Avenue - Suffern, NY

The Suffern show boasts 180 exhibitors and 13,000 – 15,000 visitors to our Street Fairs, which include Art, Crafts, Sculpture, Photography. Business and commercial exhibits. Great food, music, kid's rides, including miniature golf, bumper cars and amusements draw even more crowds to this amazing fun filled event.

Merrick Street Fair - October

October 24 - 25, 2026

nassaucountyfairs.com

(516) 442-6000

LIRR Municipal Parking Field along Sunrise Hwy - Merrick, NY

A unique family shopping destination where consumers can interact with and buy directly from the source-emerging and established local artisans and vendors. All vendors offer their handmade and handpicked items at recognizable savings. We are recognized as the #1 producer of Long Island Street Fairs and Nassau County Craft Shows. Come join us for a relaxing, unique and fun filled day!

23rd Annual Garden City South Fall Festival

October 25, 2026

(516) 317-7729

Garden City South - Garden City South, NY

23rd Annual Garden City South Fall Festival. 75 plus vendors selling unique one of a kind handcrafted items. General merchandise at great prices. Giant kids fun zone including inflatable, pony rides & a petting zoo. Great music, Fantastic food trucks and much more. Fun for the whole family. Rain Date: November 2nd.

Clwac One Hundred & Twenty-Ninth Open Juried Exhibit

October 27 - November 13, 2026

(908) 868-8749

Salmagundi Club - New York, NY

Catharine Lorillard Wolfe Art Club, Inc. 129th Annual Open Juried Exhibition at the Salmagundi Club, NY.Oct 27 - Nov. 13, 2026, Open to women artists. Media: Oil, Acrylic, Watercolor, Pastel, Drawings, Graphics, Collage, Mixed Media, and Sculpture. Near $19,000 in awards.

Eisenhower Park Field 8 Christmas Craft & Gift Fair

November 7 - 8, 2026

nassaucountyfairs.com

(516) 442-6000

Eisenhower Park Field 8 - East Meadow, NY

A unique family shopping destination where consumers can interact with and buy directly from the source-Emerging and established local artisans and high quality gift vendors. All vendors offer their handmade and handpicked items at recognizable savings.We are recognized as the #1 producer of Long Island Street Fairs and Nassau County Craft Shows. Free public admission. Enter Eisenhower Park at Field 8 for free parking.

Winter Waterway Holiday Market

November 27 - December 20, 2026

nywaterway.com

(201) 751-8782

Midtown Manhattan Ferry Terminal at Pier 79 - New York, NY

I'm Matthew Riker, I'm leading the second year of the Winter Waterway Holiday Market at our Midtown Manhattan Ferry Terminal at Pier 79. Building on what we learned from its inaugural year in 2025, I'm bringing together distinctive vendors, holiday treats, entertainment, and an inviting indoor setting. My goal is to make the terminal a memorable stop for ferry riders, tourists, and New Yorkers while creating a worthwhile opportunity for participants.

DCC Foundation Holiday Craft Fair

November 28 - 29, 2026

quailhollow.com

(845) 516-4342

Dutchess Community College - Poughkeepsie, NY

Now in its 54th year, the Dutchess Community College Foundation Holiday Craft Fair is a festive marketplace for Hudson Valley art lovers and holiday shoppers alike. The weekend-long event showcases more than 100 juried artists and makers offering fine art, ceramics, jewelry, woodwork, fiber, specialty foods, candles, soaps, and more.

Rochester International Jazz Festival

June 18 - 26, 2027

rochesterjazz.com

(585) 454-2060

Various 19 Venues - Rochester, NY

The Rochester International Jazz Festival is one of the world's leading music festivals. The festival welcomes jazz enthusiasts from around the world for nine days of extraordinary and diverse creative improvised music, hosting 1750+ of the finest artists from around the world at 300+ concerts at 19 indoor and outdoor venues, all within walking distance in Rochester's Midtown and East End Cultural Districts. Ticketed and free headliner shows, Club Pass Series shows, nightly jam sessions, and 100+ free shows and events. Food and beverages available throughout the festival.