From fair food to rides the Hudson Valley is bustling with family-friendly festivals and fairs this June. 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
June 7-8
Festival at the Falls. The festival includes entertainment & vendors in Mesier Park, tours of the Mesier Homestead, children's activities & games, sidewalk sales, restaurant specials on Main, Market, and Mill Streets, local artists & musicians performing at various spots, and the best food trucks the Hudson Valley has to offer. Wappingers Falls. 10am.
Five Points Fest. New York’s premier designer toy and indie art convention. In the spirit of merging all the titans of toys, Five Points Festival will also house the legendary Toy Pizza Expo—committed to celebrating and nurturing the best in indie toy makers, PLUS a dedicated area for Onell Design & the Glyos Universe—honoring one of the most influential modular toy systems ever created. Check out the website for all of the awesome things being offered. Beacon. 11am.
June 8
Beacon Sloop Club Annual Strawberry Festival. This favorite local event is free to the public and features two music stages, strawberry shortcake and other treats, educational displays and children's activities, and dozens of food and craft vendors. Beacon. 12pm
June 14
7th Annual Poughkeepsie Pride March and Festival. The Parade begins at the Bardavon and ends right at the festival. Over 80 local vendors, businesses, food trucks, and organizations will be tabling, sprawled throughout the park. Poughkeepsie. 12pm.
LaGrange Community Day. Live music by Jungle Love, Fireworks, Arlington High School Orchestras, Two By Two Animal Haven, Bounce Houses, Inflatable Games, Activities with Scouts, Face Painting, Strolling Entertainers, Sensory Area, Photo Ops, StoryHike, Food, Beer & Wine, Fun & Games, Community Organizations, Business Vendors & More! Food by LaGrange Lions Club under the main pavilion. Pleasant Valley. 12pm.
June 18
Juneteenth Freedom Celebration. Come together with us for a powerful day of freedom, unity, and celebration! We're honoring the spirit of Juneteenth with: Live Entertainment, Music & Dance, Food & Drinks, Fun, Games, Local Amateur Performers – including spoken word artists, dancers, and musicians! Poughkeepsie. 12pm
June 19-22
Dutchess Community Carnival Rides & Food Fair. Enjoy exciting carnival rides, classic games, tasty food, and family-friendly fun—right in the heart of the Hudson Valley! Proceeds will benefit programming through the DCC Foundation and The Chamber Foundation, Inc. Free entry, Free Parking! Poughkeepsie. Opening times vary.
June 21
Hudson Valley Food Truck Festival 2025. Experience a wide range of mouthwatering cuisine from some of the best food trucks in the area, all gathered in one place for your convenience. From savory BBQ to sweet treats, there’s something for every taste bud to enjoy. You can also enjoy live music, games, and activities for the whole family, all in a beautiful outdoor setting. Bring your appetite and your sense of adventure to this exciting event and indulge in some of the most delectable food the Hudson Valley has to offer. Poughquag. 11am.
June 25-28
LaGrange Family Carnival. As always we'll have live bands EVERY NIGHT, including fan favorites Heavy Gauge on Wednesday, Syncing Lulu on Thursday, The Red Barn Band on Friday, and Andrea and the Armenian Rug Riders on Saturday. Plus: seven awesome food vendors in addition to our own KofC food tent; games of chance; the beer garden; and of course, the rides! EVERY NIGHT IS WRISTBAND NIGHT! Lagrangeville. 6pm.
June 25
Summer Kick-off Party. Summer Break is here, and it's time to celebrate! Our Summer Kick-off Party is the perfect way to start the season with a bang! We will have a Food Truck, Bounce Houses, Crafts, and Fun games led by our Summer Camp Staff! This event is free to attend. Don't miss out on the fun! Wappingers Falls. 5pm.
June 26-July 6
Summer Carnival. Fun, food, and thrills with rides and attractions the whole family will love. There are rides for all ages. Enjoy state of the art food stands with delicious fair food like Funnel Cakes, Sausage and Peppers, Cotton Candy and so much more! Try your hand at winning a prize at one of the many games on the midway from water races to basketball games. Poughkeepsie. 5pm.
June 28
Millerton Street Fair. Live Music & Entertainment – Enjoy live music, Bee Bee the Clown, and the NECC Farmer's Market adding joy to every corner. Local Eats – Grab a bite from one of the many Millerton restaurants. Family Fun – Face painting, egg and spoon races, and a community scavenger hunt will keep the kids smiling all afternoon. Summer Reading Sign-Up – Swing by the NorthEast-Millerton Library and get your kids started on their summer reading adventure and stay for a science show. Shopping & Specials – Main Street shops will have their doors open, with some offering exclusive sales. Community Spotlights – Visit with local nonprofits showcasing their work and impact—including Eddie Collins Memorial Park, Hudson Valley Rail Trail, the NECC, North East Historical Society, The Millerton News, Townscape, Village of Millerton, Webutuck Elementary School, and more. Millerton. 10am.
Orange County
May 31-June 8
LEGO® Festival at LEGOLAND® New York Resort. Running weekends from May 3 through June 8, this epic new event invites families to build, dance, rock, and game together across five interactive Festival Zones. From rocking out at the LEGO Battle of the Bands and dancing with DJ GoodVibes to building with Master Model Builder Alec and gaming in the LEGO Fortnite zone, there's something for every young LEGO fan. 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.
June 5
9th Annual Warwick Food Truck Festival. There will be food & drinks, and live music. Warwick. 2pm.
June 7
2025 Pine Bush UFO Fair. The family-friendly event includes game and activity vendors, food and food truck vendors, and of course, UFO novelty vendors. FREE, live music, all-day entertainment, and costume contest. Pine Bush. 10am.
Kids' Day Celebration 2025. Face painting, games & activities, special giveaways (while supplies last), free food — burgers, hot dogs, snow cones & popcorn made by our awesome officers! Bring the whole family for a day full of fun, food, and community smiles. Middletown. 11am.
June 8
HV Taco Fest 8. Renowned taco trucks, restaurants, and caterers will gather to offer an extensive variety of exceptional tacos and Latin cuisine in one location. Multiple drink stations will feature ice-cold Mexican brew, Sangria, margaritas, craft beer, cider, and seltzers and Jarritos. The event will take place in the beautiful People’s Park, an ideal location to enjoy a lovely June day with family, as children under 12 years old are admitted free. Newburgh. 1pm.
June 14
Summer Fest. Live Music. Food and Beverages available on site. Includes inflatables, ground activities and foam parties throughout the day. Newburgh. 11am.
June 21
9th Annual Town of Highlands' Juneteenth Parade & Flag Raising. Parade Line up begins at 10:45 am outside of West Point's Thayer Gate on Main St, where the West Point Buffalo Soldiers Motorcycle Club will lead our March to Memorial Park, proudly holding the Juneteenth Flag. Parade/March will step off, southbound on Main Street in Highland Falls, NY and proceed down to Memorial Park for the Juneteenth Flag Raising & short program! This Year’s Honorees: Wilbur Aldridge Gato Smith & Jemika Hall. ALL ARE WELCOMED TO MARCH in the parade or drive your decorated vehicle to showcase your Juneteenth pride! Highland Falls. 11am.
Montgomery Food Truck Festival. There will be food trucks, craft vendors, activities for the kids, and live music, and fireworks. Montgomery. 11am.
Sullivan County
June 14
19th Annual Trout Parade. This year's theme of "Saturday Trout Fever" promises to be a funky, groovy time for all. This year's event will feature a Best Float & Best Costume contest. We encourage attendees to come dressed in their best disco, late-60s to 1970s attire! Livingston Manor. 10am.
June 27-29
TODDAPALOOZA 2.0. Toddapalooza is an intimate gathering of music & fun-loving Ernies at the famed Arrowhead Ranch & Retreat. Brought together for the first time in 2024 to celebrate the birthday of OG Ernie, Todd. For version 2.0, Ernie & The Band will be joined by other Long Island favorites & new jammin' Upstate friends. Parksville. 12-6pm.
Ulster County
May 31 & June 1
Rhinebeck Crafts Festival. Come shop for original fashions, accessories, jewelry, home decor, 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.
Strawberry Festival. The strawberries are plentiful for easy picking. Stop by the Tavern for our wood-fired brick-oven pizza and local wine and craft beer selection. Don’t forget our award-winning apple cider donuts! We’ll have live music all weekend including the Judith Tulloch Band on Saturday. Bring the kiddos to visit our petting zoo, take them on a tractor-pulled wagon ride and stop in Tiny Town where we have 2 new additions. Come climb on our awesome train and fire truck. Highland. 10am.
June 7
Annual Esopus Community Family Fun Day and Spring Market. Games, prizes, local vendors (farms and craftspeople) and an ice cream social are part of the day’s entertainment. Port Ewen. 10am.
June 17
Food Truck Fiesta. Live Music, Beer, Wine & Water Available. 50/50. Raindate the following Tuesday. For additional info, contact us at (845) 338-2794. Bloomington. 5pm.
June 20
Mountain Jam Festival Live music with Khruangbin, Joe Russo's Almost Dead, Kitchen Dwellers. Highmount. 2pm.
June 21
Strawberry Festival. Food, music, speakers, storytelling, activities, strawberry treats & summer fun. Ulster Park. 12pm.
Mountain Jam Festival Live music with Mt. Joy, Tramples by Turtles, Michael Franti and Spearhead. Highmount. 12pm.
June 22
Mountain Jam Festival Live music with Goose, Moe., Dogs in a Pile. Highmount. 12pm.
June 28 & 29
New Netherland Marketplace: A Living History Event 2025. Throughout this event, visitors will discover Lenape Delaware, Black, and European demonstrators sharing their craftsmanship and culture, and portraying life in mid-17th century New Netherland. New Paltz. 10am.
Other counties
June 7
Kingdom Faire 2025. 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.
June 14
Hudson River Music Festival. Rooted in the spirit of Pete and Toshi Seeger, the Hudson River Music Festival is a joyful, all-ages gathering that unites music, community, and environmental action. Fueled by a shared love for the river, it’s a soulful celebration of nature, activism, and the next chapter in a beloved tradition. Croton-on-Hudson. 12pm.
June 21
OutHudson Pride Parade and Festival! Join us in honoring the vibrant LGBTQ+ community of Columbia County and beyond with a weekend full of joy, celebration, and connection. We’re building a future where everyone regardless of race, gender, age, or ability – can live freely and authentically. Come be part of it! Pride Parade 2-3pm. March with us on Warren Street to Front Street and experience the energy, color, and love that define Hudson Pride. Pride Festival 1-4pm at Promenade Hill Park. Enjoy music, performances, vendors, food, and family-friendly fun at one of the Hudson Valley’s most scenic spots. More Events All Weekend Long! From dance parties to drag brunches, there’s something for everyone. Check out the full lineup: outhudsonny.com. Hudson. 1pm.
June 27-28
Peekskill Film Festival! Celebrate a Decade of Cinematic Excellence at the 10th Annual Peekskill Film Festival! Celebrate a Decade of Cinematic Excellence at the 10th Annual Peekskill Film Festival! Opening Night is June 27. Red carpet from 6-8pm and films from 8-11pm. Full Film Day is June 28 10am-11pm followed by an awards ceremony. Peekskill. 6pm.
Updated 6/15/2025
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