The Hudson Valley's Top Festivals and Fairs



Mark your calendar! We have rounded up of the best festivals and fairs

Top Festival and Fairs this spring in the Hudson Valley, NY
From fair food to rides and summer fun the Hudson Valley is bustling with family-friendly festivals and fairs starting in the early spring straight through the fall. We are rounding up the best festivals and fairs for 2016 and updating often so make sure you bookmark this page and check back often!

Hudson Valley Fair, May 5-21
Three weekends of fun and entertainment! The fair features rides, entertainment, fireworks and much more. Fri. 5-10pm, Sat. and Sun 12-10pm. Dutchess Stadium. 1500 New York 9D, Wappingers Falls.

2017 Kite Festival at SUNY Sullivan, May 6
Free and people of all ages are invited to SUNY Sullivan’s spacious campus to celebrate the colors of spring. 10am-4pm. SUNY Sullivan. 112 College Rd, Loch Sheldrake. 434-5750, ext. 4377.

6th Annual Cupcake Festival, May 6
Taste some of the Hudson Valley's best cupcakes and sweets, shop local vendors and fun for the whole family! 1-5pm. Main St., Beacon. 838-6000.

Hudson Valley Comic Con 2017, May 6
Sci-fi, fantasy, comics, pop culture, anime, and video games all in one expo. Upgraded Kids Zone. 10am-7pm. Gold’s Gym. 258 Titusville Rd, Poughkeepsie.

Community Connection and Business Expo, May 7
FREE Family Fun Day! 11am-2pm. The Rock Sports Park. 24 Old Black Meadow Rd, Chester. 601-522-7622.

Apple Blossom Festival & Mother's Day Picnic, May 7
Experience the orchard in bloom. Hayrides, face painting, live music, kids' crafts and activities and "touch a tractor" too. 10am-3pm. Fishkill Farms. 9 Fishkill Farm Rd, Hopewell Jct. 897-4377.

Apple Blossom Day, May 13
Face painting, bounce house, pony rides, cotton candy, lemonade, animal/flower balloons. Craft vendors, BBQ, Free Live Music and performances. 10am-4pm. Village of Red Hook. Red Hook. 750-2254.

Healthy Smiles Family Fun Day, May 13
Vendors, games, raffles and prizes, food and refreshments, a local zoo, bounce houses, K104 and much, much more! 12-4pm. Valley Pediatrics Dentistry. 1557 Route 82, Hopewell Junction. 226-8577.

Touch-A-Truck/ Family Fun Day, May 13
To raise money for local families. Interact with trucks and “Heroes” that drive them. Interactive games and other activities for families. 10am-2pm. Presidential Park Elementary School. 50 Roosevelt Ave, Middletown. 

Renegades Family Fest and Pet Expo, May 13
Up-to-date information on activities and services throughout the Hudson Valley. 11am-3pm. Dutchess Stadium. 1500 Route 9D, Wappingers Falls. 838-0094.

7th Annual Tupil Festival/ Mother's Day Celebration, May 14
Enjoy vendors, a lunch buffet and free tulip festival. 11am-4pm. Honor's Haven Resort and Spa. 1195 Arrowhead Rd, Ellenville. 210-1600.

Wildflower Festival, May 20
A full weekend for the novice and experienced gardeners. Join the HV Seed Library for an extensive collection of seedlings. 9am-5pm on Sat and 9am-4pm on Sun. Catskill Native Nursery. 607 Samsonville Rd, Kerhonkson. 626-2758.

9th Annual Millbrook Literary Festival, May 20
Join us for a celebration of authors, books and the joy of reading in the Village of Millbrook. 10am-5pm. Millbrook Library. 3 Friendly Ln, Millbrook.

Fairy Pirate Day at Museum Village, May 20
Dress up for a magical day of whimsical fun. Find the treasure, walk the plank and learn to fly! Museum Village. 1010 State Rt 17, Monroe.

Gardiner Cupcake Festival, May 20
A variety of cupcake vendors bringing in over 30,000 cupcakes. Plenty of activities for the kids including face painting, cupcake decorating, helicopter rides, pony rides, wagon rides and 5 bouncy houses. 12-6pm. Wright's Farm. 699 State Rte. 208, Gardiner. 255-5300.

Hudson Valley MayFaire, May 20
Celebrate spring and get “Lost in Neverland” with fairies, mermaids and pirates.  Plus vendors, entertainment, playground, crafts and more. Free. 10am. Robert Post Memorial Park. Kingston. 481-4182.

Hudson Valley Food Truck Festival, May 20
Local food trucks bring an array of super delicious foods, live suic, beer garden and kids entertainment. 4-9:30pm. Cantine Veterans Memorial Complex. Washington Ave, Saugerties. 399-2222.

My Kingston Kids Fest 2017, May 20
Free indoor/outdoor event created to provide children with an exlectic experience of activities, educational toold and more. RSVP. 11am-4pm. Lace Mill. 165 Cornell St, Kingston. 282-0182.

Rock Around the Clock Block Party, May 20
Vendors, food, music and much much more for families. Main St, Fishkill.

Sullivan Birth and Baby Festival, May 21
Free info sessions including prenatal yoga, breastfeeding car seat safety and safe sleep. Take a tour of the Catskill Regional Medical Birthing Center. 11am-1:30pm. Catkill Regional Medical Center. 68 Harris Bushville Rd, Harris. 794-3300.

Zerbini Family Circus at Museum Village, May 26
Jugglers, High Flyers, High Wire, Camels, Clowns and More…Purchased Tickets are good for any show! 5pm. Museum Village. 1010 State Route 17M, Monroe. 782-8248.

Spring Festival, May 27
Spend the day with family and enjoy art, crafts, music, food and fun. 10am-6pm. Downtown Sugar Loaf. 1371 Kings Hwy, Chester.

Sheep Sheering Celebration, May 29
Bring your whole entire family to relax on our lawn, breath in the fresh air and warm up in the sun while drinking wine and listening to live music. 12-6pm. Benmarl Winery. 156 Highland Ave, Marlboro. 236-4265.




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