May 1-17th: Hudson Valley Fair. One of the biggest and best family fairs in the Hudson Valley returns! Shows, music, petting zoo, rides, food, games and SO MUCH MORE! 5pm. Dutchess Stadium, 1500 Route 9D, Wappingers Falls. 845-838-0094.
May 16th: Gardiner Cupcake Festival. Live music, local food, shopping, art and craft vendors, raffles, kids’ activities, cupcake contests, and, of course, lots of yummy cupcakes. 12-6pm. Wrights Farm, 699 State Route 208, Gardiner. 845-255-5300.
May 16th: Pine Bush UFO Fair. Live music all day, fun games and attractions, a huge assortment of food, a kids section, craft vendors, UFO novelties, live characters, street performances, and the Star Wars 501st Legion Storm Troopers will be in attendance. ‘Alien and UFO Themed Parade’. 10am- 4pm. Main Street, Pine Bush. 845-744-8230.
May 16th: Spring Fling and Plow Day. Learn how the fields are prepared for spring planting. Watch the antique plows disk the fields and otheractivities and equipment on display, demonstrations and tours through the barn collections. 10am- 2pm. Orange County Farmer’s Museum, 850 State Rt. 17K, Montgomery. 845-926-2727.
May 21st: Hudson Valley Food Truck Festival. Come on out to the Hudson Valley Food Truck Festival Spring Fling! Bands and performers, great food and lots of fun. Kiwani’s Ice arena, 6 Small World Ave., Saugerties.
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May 22nd: Mysteryland Festival. Creative journey, combining music with theatre, movies, interactive installation art, street performers and shows. Times TBA. Bethel Woods Center for the arts, 200 Hurd Rd., Bethel. 866-781-2922.
May 23rd: Spring Festival. Annual Spring celebration featuring art, crafts, food, fun and music. Held rain or shine. 10am-6pm. Sugar Loaf Art and Craft Village, Sugar Loaf, Chester. 845-469-5931.
May 30th: Healthy Smiles Family Fun Day. Join us for a day of family fun! Games, raffles, fun activities, food, refreshments and a petting zoo! 12:00pm – 4:00pm. Valley Pediatric Dentistry, PC, 1557 Route 82, Hopewell Junction. 845-226-8577.
May 30th: Millbrook Literary Festival. Eighty timely, thought-provoking, and thoroughly entertaining authors and illustrators participating in panel discussions, readings, and signings throughout the day. 9:45am. Village of Millbrook, Franklin Ave., Millbrook.
May 31st: Hudson Valley Family Festival. This fun family expo provides parents with up to date information and services available in a fun environment for the entire family. 11am-3pm. Dutchess Stadium, 1500 Route 9D, Wappingers Falls. 845-838-0094.
May 31st: Family Fun Day Fest. Enjoy Live Music, bounce house village, Art Bus, kids’ activities, raffles and food. Fee. 12-6pm. Black Rock Fish and Game Club, 5 Pleasant Hill Rd., Mountainville.