From fair food to rides the Hudson Valley is bustling with family-friendly festivals and fairs this spring. We are rounding up the best festivals and fairs for the month and updating often so make sure you bookmark this page and check back often!
Dutchess County
May 17
Wappingers Central School District 75th Annual Festival of the Arts in the Park. At our 75th annual celebration, WCSD will proudly display over 10,000 works of art in a variety of genres: families can see the techniques students learn, from Kindergartners to our Advanced Placement seniors. The festival is a free, community-wide celebration of music and art, and all are welcome. Rain Date May 18, 10-4 pm. 10am. Wappingers Falls.
May 31
Rhinebeck Crafts Festival. Find handmade and uncommon items from 165+ makers you can't find anywhere else upstate! Come shop for original fashions, accessories, jewelry, home décor, furniture, photography and fine art; as well as functional and sculptural works in ceramics, glass, metal, wood, mixed media and more! Plus enjoy gourmet specialties, tastings from local distilleries, craft demos and family activities! Rhinebeck. 10am.
Orange County
May 17
A Day in the Park Adoption and Vendor Fair. Join us as we hold our first ever adoption and vendor event. Local SPCA and Humane Society’s will be on site with your next furever family member. We will have a food truck and activities for the kids. Don’t miss this event. Proceeds from this event will be split equally between the participating SPCA and Humane Society’s. We will also be collecting donations which will as well be distributed between them. Montgomery. 12pm.
May 17
Fandom Fest. Join us for an afternoon of fandom fun! Get your face painted, meet local artists, take a picture with the Rebel Legion and Empire City Garrison. Enjoy different crafts and activities based around different fandoms! This event celebrates all things pop culture for kids, tweens and teens. Cosplay is encouraged! This event is family-friendly and open to patrons of all ages, please note that while costumes are allowed, weapons, including props, are not permitted on library premises. Newburgh Free Library, 124 Grand Street, Newburgh. 1pm.
May 17-June 8 Weekends
LEGO® Festival at LEGOLAND® New York Resort. Get ready to turn up the volume on play! This epic new event invites families to build, dance, rock, and game together across five interactive Festival Zones: Music, Dance, Creative, Gaming, and Chill Out. Guests will even meet new LEGO characters, contribute to giant LEGO flower walls, and make a "Play Pact" to keep the spirit of play alive long after the day ends. Included with regular admission, LEGO Festival is the perfect way to celebrate World Play Day on June 11 and the power of creativity, exploration, and fun. Goshen. 10am.
May 24-26
Bob Dylan Tribute Festival. A day dedicated to the music of Bob Dylan. 12pm to 5pm each day. No dogs, no coolers, no outside food or alcoholic beverages. Tickets will be held for you at the door. No tickets will be mailed. Outdoor festivals are performed rain or shine unless otherwise specified. Warwick. 12pm.
May 24
Memorial Day Vendor & Craft Market at HVSPCA. Over 70+ vendors & artisans coming together, there is literally something for everyone in the family! Bring them all along for a day out of eating, drinking, shopping and, of course...plenty of wonderful dogs and cats looking for their forever homes!! If you are interested in adopting a new furry family member, please go to www.hudsonvalleyspca.com to get your adoption application. New Windsor. 10am.
May 24-25
Sugar Loaf Spring Festival. There will be unique artisan shoppes showcasing one-of-a-kind creations, vendors with a variety of amazing finds, family-friendly activities: Face painting, petting zoo, bouncy houses, and a kids' zone, food trucks, beer garden, wine bar, and tastings for the adults. Live music. Dog-friendly. Sugar Loaf. 10am.
Sullivan County
May 17
TSTS (Too Short to Suck) Film Festival and Awards Show. An annual celebration of storytelling through short films, showcasing works that are 2 minutes or less in duration. The event culminates in an awards show recognizing the best in several categories, including Best Cinematography, Best Animation, and Judges’ Award. Held annually in Parksville, NY, TSTS fosters creativity, community, and collaboration, providing a platform for local filmmakers to share their work and connect with fellow artists. Parksville. 6pm.
May 26
Memorial Day Parade. A day to reflect and remember our service members who gave the ultimate sacrifice for us and our nation. Line-up 9:30 @ Livingston Manor firehouse Parade step off 10am, ceremony to follow on Pearl Street at memorial site. Livingston Manor. 10am.
May 30-June 1
Spring Fest at Main Camp. Discover Frost Valley in full bloom this spring! Celebrate spring with us through activities such as environmentally friendly plant print pottery, campfire cooking, boating, and a lively all-camp gathering featuring lawn games, contests, and line dancing. Build connections, foster friendships, and unplug with nature for an unforgettable weekend experience. Claryville. 4pm.
Ulster County
May 17
2nd Annual Hudson Valley Kite Fest. Get ready to soar at Kingston’s 2nd Annual Hudson Valley Kite Fest! Whether you’re a seasoned flyer or a first timer, this free, family-friendly event is the perfect place to experience the joy of kites. Bring your own or purchase and design one on-site—then watch it take flight over Kingston Point Beach! The festival will feature a variety of vendors, live performances, and the MyKingstonKids Play Cafe, offering something for everyone. Enjoy delicious food, shop unique finds, and experience so much more—all while soaking in the vibrant atmosphere of the day. Kingston. 11am.
May 20
Food Truck Fiesta. Live Music, Beer, Wine & Water Available. 50/50. Rain date the following Tuesday. Bloomington. 5pm.
May 23
Ashokan Uke Fest 2025. Expand your skills or capture the aloha spirit of the ukulele for the first time at the Ashokan Ukulele Weekend! There’ll be workshops for all levels, a staff concert, group strums, a Camper Cabaret open mic, and lots more ukulele fun and camaraderie! You’ll meet new people, learn new techniques and styles, and gain confidence as a player. Olivebridge. 3pm.
May 24-26
Woodstock-New Paltz Art & Crafts Fairs. The Woodstock-New Paltz Art & Crafts Fair has evolved into a highly successful event, voted one of the top art and craft shows in America by Sunshine Artist Magazine. 200 juried artists and makers, craft demonstrations, entertainment, specialty foods, and children's entertainment. New Paltz. 10am.
May 25
Town of Marlborough Memorial Day Parade. The theme for this year's parade is “Flags of Honor” honoring all Veterans & commemorating the 50th Anniversary of the Vietnam War. Parade participants will assemble at the Marlboro High School, 50 Cross Road, Marlboro at 12pm. The parade kicks off at 1pm and concludes at Marlboro Elementary School on 9W. Marlboro. 12pm.
May 30-June 1
Field + Supply Spring MRKT. Join us for Spring MRKT 2025 to shop hundreds of vendors. Plus, enjoy live music, local eats, and activities for the entire family. Discover thousands of products from the most talented makers, artisans, and independent designers in the country. Kingston. 10am.
Other Counties
May 31
FASNY Museum Centennial Celebration. Join us to celebrate the Museum’s 100th birthday! This half-day event includes a performance by The Ghent Band, the opening of a new exhibit. All activities are FREE, and FREE admission to the Museum will also be offered to all who attend this special anniversary event. Come party with us as we celebrate 100 years! The FASNY (The Firefighters Association of the State of New York) Museum of Firefighting, 117 Harry Howard Avenue, Hudson. 10am.
May 31
Kingdom Faire 2025. Kingdom Faire: An Adventure Awaits! Step into a world of fantasy, adventure, and excitement. Immerse yourself in a realm where daring heroes, cunning rogues, and mystical beings come to life through live performances, thrilling battles, and interactive storytelling. Join us for a weekend of adventure where legends are made, and destinies are forged! Secure your tickets now and prepare to enter the realm of Kingdom Faire! Putnam Valley. 10am.
Updated 5/13/2025
Other articles by HVP Top Lists