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Roll out the rainbow flag and celebrate Pride Month in Peekskill this June. Photo courtesy of Peekskill Pride
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5/26/23 - By Susan Miele

Summer fairs and festivals in Westchester and the Hudson Valley offer a ton of ways to party al fresco this summer. While outdoor fun can reliably be found at area beaches or campgrounds, the region's staged outdoor entertainment options are wide-ranging, including picnic-blanket music festivals and cultural-heritage feasts.

We are kicking off the summer festivities with the family-friendly Scarsdale Music Festival and a Juneteenth Kickoff Festival in New Rochelle. Other stand-out events include a Sangria Festival at Benmarl Winery and the annual Bear Mountain Native American Heritage Celebration and Pow Wow.

Looking for even more family-friendly activities? Consult our Event Calendar and Summer Fun Guide, and sign up for our newsletters to get posts like this delivered to your inbox.

More Free Activities in the Hudson Valley this Summer

Free Summer Concerts | Free Summer Movies | Free Activities

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Travel back in time to Elizabethan England at the New York Renaissance Faire. Photo courtesy of the event
Travel back in time to Elizabethan England at the New York Renaissance Faire. Photo courtesy of the event

Summer Fairs and Festivals in Westchester and the Hudson Valley in June 2024

Scarsdale Music Festival

Scarsdale–FREE
Sunday, June 1, 2024
Enjoy a day of live music and fun for all ages at the 4th annual Scarsdale Music Festival. This year's festival features bands from Scarsdale and the tri-state area on two main stages as well as an acoustic stage, a Grand Tasting Village for adults 21+, food trucks and other food vendors, and an enhanced family fun zone featuring carnival games, face painters, arts and crafts, musical demonstrations, DIY and STEAM activities, sports, inflatables, and more! READ MORE

Tarrytown Craft, Food and Street Fair

Tarrytown–FREE
Sunday, June 1, 2024
Peruse the wares of some 100 vendors and crafters while enjoying local food, beverages, live entertainment, and kids' activities along Tarrytown's Main Street. READ MORE

Juneteenth Kickoff Festival at New Rochelle Boys & Girls Club

New Rochelle–FREE
Saturday, June 1, 2024
Break bread with the Westchester & Rockland Juneteenth Coalition in celebration of the first African American Holiday! Enjoy traditional foods prepared by award-winning Chef El-Amin, an original play about Juneteenth, historical reenactments, music & dance performances, kids' activities, an exhibit on the history of Juneteenth, and much more! READ MORE

Nanuet Street Fair

Nanuet–FREE
Sunday, June 2, 2024
The Nanuet Street Fair features more than 170 vendors plus live music, kids' activities, food, and a car and Jeep show.  READ MORE

RiverFest in Cornwall's Donahue Park

Cornwall-on-Hudson–FREE
Sunday, June 2, 2024
Held on the scenic shores of the Hudson River in Donahue Park in Cornwall-on-Hudson, this annual festival features assorted entertainers as well as live music, food, vendors, kids' crafts, and activities.  READ MORE

West Nyack Greek Festival

Nyack
Thursday, June 6-Sunday, June 9, 2024
The Annual West Nyack Greek Festival features Greek foods & desserts, live music and dancing, rides & games, and shopping at the Saints Constantine and Helen Church. READ MORE

Fol de Rol County Fair

Armonk
Thursday, June 6-Sunday, June 9, 2024
Now in its 48th year, this county fair, hosted by the Armonk Lions Club, features games, carnival rides, food, craft vendors, a pet parade, a car parade, music and more. Proceeds support the Lions' charitable endeavors.  READ MORE

Festa Italiana in West Harrison

Harrison–FREE
Friday, June 7-Sunday, June 9, 2024
Celebrate Italian heritage all weekend long at Saint Anthony of Padua Church's annual festival. Enjoy Italian food, children's activities, games, and more.  READ MORE

Yonkers Greek Food Festival

Yonkers
Friday, June 7-Sunday, June 9, 2024
This three-day festival celebrating Greek culture includes food, live Greek music, folk dancing, a kids' zone, games, and more. The fun at this fest extends well past bedtime! Bring your appetite. READ MORE

Beacon Strawberry Festival at Pete and Toshi Seegar and Riverfront Park

Beacon–FREE
Sunday, June 9, 2024
Enjoy an old-fashioned strawberry festival to celebrate the arrival of spring, with live music on two stages, strawberry shortcake, arts and crafts vendors, children's activities, and more fun in Pete and Toshi Seegar and Riverfront Park on the Hudson River.  READ MORE

Rockland Pride Sunday Festival in Downtown Nyack

Nyack–FREE
Sunday, June 9, 2024
Now in its 25th year, Rockland Pride Sunday is back in-person for a day filled with music, dancing, and pride. This free family-friendly event in downtown Nyack features live music, drag queens, outdoor dining, shopping, vendors, and more. Free children's activities include bounce houses, face painting, and an arts and crafts tent. READ MORE

Yonkers Ukrainian Heritage Festival

Yonkers–FREE
Friday, June 14-Sunday, June 16, 2024
Sponsored by the Ukrainian American Youth Association, this annual tradition brings Ukrainian food, culture, music, dancing, crafts, and traditions to Yonkers, along with carnival rides and games, plus assorted vendors.  READ MORE

Hudson Valley Food Truck Festival at Barton Orchards

Poughquag–FREE
Saturday, June 15, 2024
Sample a range of dishes from diverse food trucks and vendors with live music and a farm market at Barton Orchards in Poughquag. Activities for kids include a petting zoo, gem stone mining, a dog park, and wooden playground. The tap room and restaurant are also open.  READ MORE

Village of Pelham Juneteenth Celebration

Pelham–FREE
Sunday, June 16, 2024
The Village of Pelham invites you to a day of inspiration, education, cultural connection, and entertainment as we honor and celebrate the Juneteenth Federal Holiday. Enjoy live entertainment, food, art, dancing, a DJ, and more! READ MORE

Poughkeepsie Greek Festival

Poughkeepsie–FREE
Friday, June 21-Sunday, June 23, 2024
Expect feasting, entertainment, and insights into Greek culture at this multi-day festival. Immerse your family in Greek culture with Greek music, food, performances, and dancing. Children's activities are also on the agenda, including a bouncy house, and vendors sell their wares. READ MORE

American Roots Music Festival at Caramoor

Katonah
Saturday, June 29, 2024
Tickets are available for theater seating or on the lawn outside, where attendees can bring a blanket or beach chair and enjoy daytime performances by numerous artists on multiple stages. Pack a picnic or purchase food on-site. The grounds alone are worth the visit. READ MORE

Peekskill Pride in Pugsley Park

Peekskill–FREE
Saturday, June 29, 2024
Join Peekskill Pride for its 4th Annual Family Pride in Pugsley Park, with live bands, drag shows, and family-friendly activities including arts & crafts and drag queen storytime.  READ MORE
Groove to the Caramoor Jazz Festival. Photo courtesy of Caramoor
Groove to the Caramoor Jazz Festival. Photo courtesy of Caramoor

Summer Fairs and Festivals in Westchester and the Hudson Valley in July 2024

Pleasantville Music Festival

Pleasantville
Saturday, July 13, 2024
This festival combines the feel of a small-town, outdoor concert with nationally recognized musicians. Vendors, food, kid activities, like bouncy houses and a rock wall, plus nine hours of music on three stages round out the festivities. Headlining acts include Better than Ezra, The Wailers, and more. READ MORE

Bear Mountain Native American Heritage Celebration and Pow Wow

Pleasantville
Saturday & Sunday, July 13 & 14, 2024
Check out a real teepee, play with Native American instruments, try some foods popular in Native American cultures, and take in a dance performance by Native American groups from throughout the Americas. Dancers make their grand entrance for shows at 1pm and 5pm.  READ MORE

Warwick Food Truck Festival

Warwick
Thursday, July 18, 2024
The Warwick Food Truck Festival takes place each summer in the beautiful town of Warwick, NY. Get ready for food-truck fare, desserts and sweets, locally crafted brews, live music, and more! The new location this year is Warwick's Mountain Lake Park. READ MORE

Orange County Fair

Middletown
Thursday, July 18-Sunday, July 28, 2024
The annual Orange County Fair returns, featuring new carnival rides, a performance by the Anastasini Circus, monster truck shows, a petting zoo, fireworks, and more. READ MORE

Sangria Festival at Benmarl Winery

Marlboro
Saturday & Sunday, July 20 & 21, 2024
Enjoy live music, sangria tasting, food, and dancing all day at Benmarl Winery's Sangria Festival. There will be live music by Ola Flamenca and Flamenco dancing lessons for the whole family. READ MORE

Otisville Country Fair

Otisville
Thursday, July 25 - Sunday, July 28, 2024
This good old-fashioned country fair has a hay-bale toss, a chainsaw competition, horseshoe tournament, car show, tractor pull, cast-iron frying-pan toss, hayrides, antique machinery, storybook princess parties, animal tent, and food.  READ MORE

Caramoor Jazz Festival

Katonah
Saturday, July 27, 2024
Caramoor joins forces with Jazz at Lincoln Center to provide a day full of live music on its bucolic grounds. Pack a picnic or purchase food on-site, and stroll the lovely gardens.  READ MORE
Watch the sky fill with balloons at the Hudson Valley Hot Air Balloon Festival. Photo courtesy of the festival
Watch the sky fill with balloons at the Hudson Valley Hot Air Balloon Festival. Photo courtesy of the festival

Summer Fairs and Festivals in Westchester and the Hudson Valley in August-September 2024

Ulster County Fair

New Paltz
Tuesday, July 30-Sunday, August 4, 2024
This 6-day fair–steeped in more than 130 years of history–offers rides, food, entertainment, exhibits, and games in traditional county-fair style. Listed attractions include racing pigs, fireworks, a baby contest, horse shows, stilt walkers, a petting zoo, and other assorted fun. READ MORE

Beacon Corn Festival

Beacon–FREE
Sunday, August 11, 2024
This festival, hosted by the Beacon Sloop Club, celebrates all things corn at the Beacon Riverfront Park. Expect live music, food, craft vendors, and free kids’ activities. READ MORE

Saugerties Caribbean Carnival & Parade

Saugerties–FREE
Saturday, August 17, 2024
Experience the festive culture of the Caribbean at this fun, family-friendly carnival with face painting, a costume contest, DJ, arts & crafts, food vendors, and more, plus a colorful parade. READ MORE

New York Renaissance Faire in Tuxedo

Tuxedo
Weekends from Saturday, August 17-Sunday, October 6, 2024
Also on Labor Day
Travel back in time for an amusing romp through 30 acres of Elizabethan England, with games, rides, food, fairies, performances, and roving actors jovially interacting with the crowd. Of course, wearing period attire adds to the fun and can be rented or purchased on-site. READ MORE

Dutchess County Fair

Rhinebeck
Tuesday, August 20-Sunday, August 25, 2024
This large-scale fair features Midway carnival rides, games, livestock exhibits, competitions, and a slew of entertainment that ranges from racing pigs and dock-diving dogs to chainsaw carving and a tractor pull. The fair features a petting zoo, kids' fun zone, acrobats, concerts, and much more. READ MORE

Hudson Valley Hot Air Balloon Festival

Union Vale
Friday, August 30-Sunday, September 1, 2024
Plan your next photo-op as some 75 hot-air balloons paint the sky in a rainbow of colors —or schedule a tethered or full flight of your own. Fireworks, helicopter rides, live music, food trucks, and family activities add to the fun. READ MORE

Woodstock-New Paltz Art & Crafts Fair at Ulster County Fairgrounds

New Paltz
Saturday, August 31-Monday, September 2, 2024
Held twice yearly—Memorial Day and Labor Day weekends—this fair showcases the work of more than 200 artists from across the United States at the Ulster County Fairgrounds. The children's tent features demonstrations and supervised arts and crafts projects. Live entertainment and activities are planned. READ MORE

Places featured in this article:

Scarsdale Village Center
Boys & Girls Club- New Rochelle
Saints Constantine and Helen Church
Pete and Toshi Seegar and Riverfront Park
Caramoor Center for Music and the Arts
Anthony Wayne Recreation Area at Harriman State Park
Caramoor Center for Music and the Arts
Beacon Riverfront Park