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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. There are also longstanding agricultural fairs that offer everything from carnival rides to racing pigs. Below, we’ve gathered more than two dozen summer festivals worth adding to your calendar.

New additions to this year's lineup include a pro-wrestling festival as well as family-friendly celebrations of Pride Month and Juneteenth. 

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 2023

West Nyack Greek Festival

Nyack
Thursday, June 1-Sunday, June 4, 2023
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

Festa Italiana in West Harrison

Harrison–FREE
Friday, June 2-Sunday, June 4, 2023
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

Tarrytown Craft, Food and Street Fair

Tarrytown–FREE
Sunday, June 4, 2023
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

Nanuet Street Fair

Nanuet–FREE
Sunday, June 4, 2023
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 4, 2023
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

Fol de Rol County Fair

Armonk
Thursday, June 8-Sunday, June 11, 2023
Now in its 47th 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. New in 2023: hot air balloon rides from 6-10pm on Thursday and Friday, 6/8 and 6/9.  READ MORE

Greek Food Festival

Yonkers
Friday, June 9-Sunday, June 11, 2023
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

White Plains Juneteenth Parade and Festival

White Plains–FREE
Saturday, June 10, 2023
Celebrate Juneteenth with a parade featuring bands, dancers, drummers, music, stiltwalkers, and more with a festival afterward including entertainment, vendors, and food.  READ MORE

Beacon Strawberry Festival at Pete and Toshi Seegar and Riverfront Park

Beacon–FREE
Sunday, June 11, 2023
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

Nyack–FREE
Sunday, June 11, 2023
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, the crowning of Mx. Rockland County Pride, 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 16-Sunday, June 17, 2023
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. Proceeds go toward Ukrainian relief organizations. READ MORE

Juneteenth Celebration - Mamaroneck

Mamaroneck–FREE
Saturday, June 17, 2023
Join OneMamaroneck for a celebration of Juneteenth in Columbus Park, featuring food trucks, song and dance performances, drumming, face painting, a basketball tournament, and more. Guests repaint the Black Lives Matter street mural. READ MORE

Poughkeepsie Greek Festival

Poughkeepsie–FREE
Friday, June 23-Sunday, June 25, 2023
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

Katonah
Saturday, June 24, 2023
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

Hudson Valley Food Truck Festival at Barton Orchards

Poughquag–FREE
Saturday, June 24, 2023
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

Peekskill Pride in the Park

Peekskill–FREE
Saturday, June 24, 2023
Join Peekskill Pride for its 3rd Annual Family Pride in Pugsley Park, with live bands, drag shows, and family-friendly activities.  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 2023

Annual Great American Weekend

Goshen–FREE
Saturday, July 1-Sunday, July 2, 2023
This two-day annual tradition, organized by the Goshen Chamber of Commerce, features some 150 craft booths, live entertainment, children's activities, and extensive food choices.  READ MORE

Pleasantville Music Festival

Pleasantville
Saturday, July 8, 2023
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 They Might Be Giants, The Allman Betts Band, Sophie B. Hawkins, and more. READ MORE

Orange County Fair

Middletown
Thursday, July 20-Sunday, July 3 0, 2023
The annual Orange County Fair returns for the 183rd year, featuring new carnival rides, a performance by the Anastasini Circus, monster trucks, a petting zoo, fireworks, and more. READ MORE

Caramoor Jazz Festival

Katonah
Saturday, July 22, 2023
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

Food, Music, & Pro Wrestling Festival

Pine Island
Saturday, July 22, 2023
Don't miss this music, food, and pro-wrestling festival at one of the most eclectic animal rescue farms in the tri-state area. Highlights include food trucks, live music, pro-wrestling shows, and lots of kids' activities, including a bounce house. READ MORE

Otisville Country Fair

Otisville
Thursday, July 27 - Sunday, July 30, 2023
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
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 2023

Ulster County Fair

New Paltz
Tuesday, August 1-Sunday, August 6, 2023
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

Putnam County Wine & Food Fest

Brewster
Saturday, August 5-Sunday, August 6, 2023
Grab your blanket and chairs and celebrate the 12th anniversary of the Putnam County Wine & Food Fest with wine, spirits, live music, craft vendors, and cooking and mixology demonstrations. Kids' activities include face painting, rides, sand art, and other games. READ MORE

Beacon Corn Festival

Beacon–FREE
Sunday, August 13, 2023
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

Hudson Valley Jazz Festival

Multiple locations
Wednesday, August 9-Sunday, August 13, 2023
The Hudson Valley Jazz Festival returns for its 14th year with four days of performances scattered around the Hudson Valley at various venues in Greenwood Lake, Warwick, Sugar Loaf, and other communities. Most performances listed are FREE. READ MORE

Caribbean Carnival & Parade

Saugerties–FREE
Saturday, August 12, 2023
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

Dutchess County Fair

Rhinebeck
Tuesday, August 22-Sunday, August 27, 2023
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

New York Renaissance Faire

Tuxedo
Weekends from Saturday, August 26-Sunday, October 8, 2023
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

Hudson Valley Hot Air Balloon Festival

Union Vale
Friday, September 1- Sunday, September 3, 2023
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, September 2-Monday, September 4, 2023
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:

Saints Constantine and Helen Church
Pete and Toshi Seegar and Riverfront Park
Caramoor Center for Music and the Arts
First Presbyterian Church Park
Caramoor Center for Music and the Arts
Beacon Riverfront Park