May 2025: Fairs and Festivals in and around Westchester County 🎡🎠🎪
May is here, and it's packed with amazing festivals throughout Westchester County and neighboring areas. We're excited to share some of our favorite upcoming events that we think you'll love. These include a fun mix of music festivals, food celebrations, street fairs, cultural events, and art showcases.
This month offers plenty of opportunities to explore, taste, listen, and experience the best of what the area has to offer. And this is just the beginning—we'll be bringing you our most anticipated summer festivals for the remaining summer months, so you can plan for a season full of fun!
Don't hesitate to leave a note in the comments if we missed a fun one for the month of May!
Music Festivals 🎸🎷🪕
Montauk Music Festival
Montauk, Long Island, NY
Thursday, May 15 - Sunday, May 18
Fairfield Hills Music Festival
Newtown, CT
Saturday, May 17
Dance Parade
Manhattan, NY
Saturday, May 17
Hudson Valley Hoedown Street Festival
Croton-On-Hudson, NY
Saturday, May 17
Bluegrass Festival
Woodstock, NY
Saturday, May 24
FOOD Festivals 🍖🍷🍜
Japan Fes
Upper West Side, Manhattan
Sunday, May 4
Rip Van Winkle Wine, Brew & Beverage Festival
Catskill, NY
Saturday, May 10
Japan Fes
Chelsea, Manhattan
Saturday, May 10
Ninth Avenue International Food Festival
Manhattan, NY
Saturday, May 17 - Sunday, May 18
Mineola Foodie Festival
Wilson Park, Mineola, Long Island, NY
Saturday, May 17 - Sunday, May 18
Japan Fes
Park Slope, Brooklyn
Sunday, May 18
Hudson Berkshire Wine and Food Festival
Columbia County Fairgrounds, Chatham, NY
Saturday, May 24 - Sunday, May 25
Cultural Heritage Festivals 🥁👹🥘
Pinkster Jubilee 2025
Yonkers, NY
Saturday, May 10
Asian American Pacific Islander Festival
Ardsley, NY
Saturday, May 17
Holi Festival of Colors
Broadway Field, Hawthorne, NY
Saturday, May 17
Polish Heritage Day
Kensico Dam Plaza, Valhalla, NY
Sunday, May 18
Asian American Heritage Festival
Kensico Dam Plaza, Valhalla, NY
Saturday, May 31
Art Festivals 🎨 👩🎨🎬
The Spring Craft Show
Tarrytown, NY
Friday, May 2 - Saturday, May 3 - Sunday, May 4
Art Lives Here
New Rochelle, NY
Saturday, May 10
The 1 - 54 Contemporary African Art Fair
Manhattan, NY
Thursday, May 8 - Friday, May 9 - Saturday, May 10 - Sunday, May 11
Yonkers Art Weekend
Yonkers, NY
Saturday, May 18 - Sunday, May 19
Woodstock-New Paltz Art & Crafts Fair
New Paltz, NY
Saturday, May 24 - Sunday, May 25 - Monday, May 26
Port Chester Arts Festival
Port Chester, NY
Saturday, May 31
Artrider's: Rhinebeck Craft Festival
Rhinebeck, NY
Saturday, May 31
Street Fairs and Festivals 🍔🎪🥨
Jefferson Valley Mall Carnival
Yorktown Heights, NY
Ongoing until Sunday, May 4
Rhinebeck Antique Car Show & Swap Meet
Rhinebeck, NY
Friday, May 2 - Saturday, May 3 - Sunday, May 4
Shop Small Biz Street Fair
Manhattan, NY
Saturday, May 3
Peekskill Cherry Blossom Festival
Peekskill, NY
Saturday, May 3
Columbus Circle Spring Fair
Manhattan, NY
Saturday, May 3 - Sunday, May 4
Apple Blossom Children’s Carnival
Queens County Farm Museum, Floral Park, Queens, NY
Saturday, May 3 - Sunday, May 4 - Saturday, May 10 - Sunday, May 11
Hudson Valley Fair
Heritage Financial Park, Wappingers Falls, NY
Wednesday, May 7 - Sunday, May 11
Suds on the Sound
Rye, NY
Saturday, May 10
Avenue of the Americas Shopping Spectacular
Manhattan, NY
Saturday, May 10
Woodside Festival
Queens, NY
Saturday, May 10
Albany Tulip Festival
Albany, NY
Saturday, May 10
Broadway Lincoln Square Fair
Manhattan, NY
Sunday, May 11
The Hastings Record Riot PLUS!
Hastings, NY
Sunday, May 18
Nyack Street Fair
Nyack, NY
Sunday, May 18
Fabulous 5th Ave Fair 2025
Brooklyn, NY
Sunday, May 18
Lexington Avenue Spring Fest
Manhattan, NY
Sunday, May 18
Sheep and Wool Festival
Chestnut Ridge, NY
Sunday, May 18
Mayfest Farmers and Makers Market
Highland, NY
Saturday, May 24
Spring Antiques At Rhinebeck
Rhinebeck, NY
Saturday, May 24 - Sunday, May 25
LIC Springs!
Long Island City, Queens, NY
Saturday, May 31
We hope you get to enjoy a few of the fairs and festivals taking place during the month of May. Stay tuned for part 2, which will cover the month of June.
Happy adventuring!
