Your Complete Guide to Summer Events in the Hudson Valley

Now that the cold weather is finally gone, it’s time to enjoy all the Valley’s spectacular summer activities

Dutchess County Fair. Photo by Maureen Gates,

From art to food to music to theater, these fairs, fests, and fun events will keep you busy all season long.

By Francesca Furey, Jake Mauriello, and Megan Wilson

– Festivals –

June 25–28: Round Top Bavarian Summer Fest

Say “guten tag” to a fun taste of Germany deep in the Catskills. Riedlbauer’s Resort presents this annual festival at their Nussy’s Bier Garten, brimming with classic, Bavarian-style live music and dancing, juicy schnitzel and brats, and tons of beer.

Round Top;

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June 26–27: Rhinebeck Crafts Festival

Get your craft on! Tucked away in a creative capital of the Valley, Artrider’s two-day festival celebrates artists and handmade fine arts and crafts. Head to the Dutchess County Fairgrounds to shop for unique pieces and sample products from gourmet concessions, local wineries, and distilleries.


August 7–8: Putnam County Wine & Food Festival

Calling all beginner and expert sommeliers! Celebrating its 10th anniversary, this annual festival heads to Mayor’s Park in Cold Spring for two days of live music, wine and spirit tastings, chef demonstrations, art and crafts, and various exhibits. The festival is rain or shine.

Cold Spring,

August 14: New York Snow Crab Festival

Love seafood? This only-one-of-its-kind-in-the-Valley festival focuses on delectable Alaskan Snow Crab. There are also fun lawn games, polo matches, a dance floor, and hot-air balloon viewing.

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August 18–22: Nyack Film Festival

For its 9th year, this film festival presents a movie buff’s paradise, with national and international submissions of cinematic glory. What makes it so unique — and fun for Valley residents — is the large number of local films shown over the course of the three-day event.


Hudson Valley Hot-Air Balloon Festival. Photo courtesy of Dutchess County Regional Chamber of Commerce

September 3–5: Hudson Valley Hot-Air Balloon Festival

For its 30th year in action, this famed festival is coming to Tymor Park. Bring friends or family and a picnic as you watch colorful balloons float across the sky. Buy tickets (viewing only, due to COVID protocols) in advance to close out your summer with breathtaking day views and an illuminated night sky, plus access to various vendors.

Union Vale;

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– Theater –

June 24–Sept 6: Hudson Valley Shakespeare Festival

The iconic festival takes the stage at Boscobel for the last time this summer, before moving to its new Philipstown location in 2022. Spend a summer night with a production of Shakespeare’s drama The Tempest (Aug 5–Sept 4). Plus, earlier in the season, enjoy James Ijames’ contemporary play about the legacy of slavery in America, The Most Spectacularly Lamentable Trial of Miz Martha Washington (Jun 24–Jul 30). Both productions will occur under an open-air tent at Boscobel House and Gardens.


July 16: PS21 presents “Pan”

It’s been too long without Broadway; Here’s something to tide over theater geeks. Led by MacArthur Fellow flute soloist Claire Chase, “Pan” is described as a “celebration of the post-pandemic rebirth, nature and community” that details the life of the titular Greek deity and connects it to contemporary life. This live performance is held at PS21’s open-air Pavilion Theater.


– Music –

June 6–September 1: City Winery Hudson Valley’s Summer Concert Series

The Concerts in the Vineyard series kicks off on June 6 with a show by Damn the Torpedoes: A Live Tom Petty Experience. Other acts throughout the summer include: Southside Johnny & The Asbury Jukes (June 19), 10,000 Maniacs (June 26), Joan Osborne (July 11). Seating for all shows will be in pods to ensure safe social distancing, and proof of vaccination or a negative Covid-19 test is required for entry.


June 19: The Great Hudson River Revival

The Clearwater Festival is normally a huge celebration of environmental activism, featuring famed musicians, public figures, and the beloved Sloop Clearwater sailboat. This year, the festival will be live streamed on Clearwater’s website, Facebook, and YouTube pages. Tune in for passionate speeches, performances, and more.


Natu Camara, Caramoor Summer Music Festival. Photo by Jamie Ambler

June 19–August 8: Caramoor Summer Music Festival

With performers spanning a multitude of musical genres and cultural backgrounds, jam out to 35 live events throughout the summer season. Enjoy season highlights like the annual Jazz Festival, Pops & Patriots Concert, or a celebration of Stephen Sondheim’s 91st birthday, all held outdoors on Caramoor’s grounds in Westchester.


Bethel Woods Concerts

Featuring events rescheduled from 2020, the Bethel Woods Pavilion concert series presents outdoor shows throughout July and August on the land where the famous 1969 Woodstock Festival took place. Tickets purchased for the original 2020 dates will be honored.

July 2: James Taylor
July 4: Steely Dan with Steve Winwood
July 10: The Black Crowes
July 20: An Evening with Chicago
August 19: Kidz Bop
August 22: Santana with Earth, Wind & Fire


– Art –

Through November 8: The Russel & Mary Wright Design Gallery at Manitoga

After a seemingly endless year, this architectural monument has re-opened its doors. Find more than 200 objects designed by the Wrights specifically for Manitoga. (The Design Gallery is included in public tours of the site.) Architecture and design aficionados can also explore the home, studio, woodland garden, and gallery through guided tours.


Pollinator Pavilion. Photo by Peter Aaron/Otto

June 12–Oct 31: Cross Pollination: Heade, Cole, Church, and Our Contemporary Moment

Escape to the beauties of nature in the form of art at the Olana and Thomas Cole historic sites. Stemming from 19th-century hummingbird and habitat paintings by Martin Johnson Heade, this presentation explores crosspollination in both art and nature, featuring work from artists spanning the 1800s to now. The exhibition is open until Halloween.


July 12–18: Virtual Taste of Catskills Irish Arts Week

Become a student again at this virtual taste of Irish arts, with access to a variety of masterclasses in Irish instruments, language, literature, and dancing. Participants are also able to view prerecorded presentations and concerts of past Irish celebrations. Perhaps with some four-leaf clover luck, this Irish Alps event will return to the Catskills next year.


– The Animal Kingdom –

Through September 12: HITS-on-the-Hudson Saugerties Series

Get up close and personal with beautiful, pedigree horses. For nine weeks, HITS welcomes equestrians for several competitions of varying difficulty. Come as a spectator to watch horses and their riders make impressive maneuvers and exciting jumps in Olympic-level horse shows.


June 5: Birds! A Nature Walk with Ethnoecologist Justin Wexler

What a hoot! Get a peak at the area’s migratory and resident birds on this walk starting at the replica Esopus Munsee wigwam on New Paltz’s historic Huguenot Street. As you’re led to the Nyquist-Harcourt Wildlife Sanctuary, hear about indigenous bird folklore and names, plus some history of bird life.

New Paltz;

Lyndhurst Estate. Photo by Clifford Pickett

June 11–13: Westminster Dog Show

Held outside at the Lyndhurst Estate, the 145th annual Westminster Kennel Club Dog Show will be paw-some. Attendance will be virtual due to COVID-19; dog lovers can coo over cute and talented pups on FOX Sports networks. Tune in for Best in Show judging on the 13th.


– On Wheels

Farm to Fork Fondo. Photo courtesy of Farm to Fork Fitness Adventures

July 10: 2021 Farm to Fork Fondo

Limited to 250 participants, this organized bike ride is a real “choose your own adventure,” with distances ranging from a 10-mile to a 75-mile ride. Along the way, stop at Hudson Valley farms to sample small bites and learn about the agriculture in the Valley. End your day with a much-needed organic picnic lunch.

New Paltz;

June 12: The Catskill Conquest Covered Bridge Rally

For its second year, this rally of vintage cars commemorates the 1903 Automobile Endurance Run that once wound through the Catskills. Spanning 140 miles roundtrip and passing through Ulster, Sullivan, and Delaware Counties, drivers can awe in rural views, smooth roads, and 13 historic covered bridges. Plus, refreshments and browsing at the route’s end in the Town of Andes.

Mount Tremper/Andes;

July 11: Sawyer Motors’ 17th Annual Car Show

This beloved car show has returned: check out more than 500 hot rods, muscle cars, and classic antique vehicles lining the streets of Saugerties. Vibe to entertainment on four different stages while strolling by cars you wish were in your own garage. The Sawyer Automotive Foundation donates a percentage of proceeds to local charities.


August 14: 14th Annual “Tour of the Catskills” Pro-Am Bicycle Road Race

With up to 500 spots available this year, cycle in the heart of the scenic Catskills. There are three races of varying degrees of difficulty: 27-, 52-, or 75-mile rides. Challenge yourself by tackling the famous Devil’s Kitchen Climb, included in the 75-mile registration.


– County Fairs –

July 15 – August 1: Orange County Fair

It’s all about the engines at the Orange County Fair, where you’ll find the best vehicular entertainment from monster trucks to the demolition derby. Apart from its unique taste in carnival fun, this event still maintains its county fair feel with traditional and thrill-seeking rides and other entertainment.


July 22 – 25: Greene County Fair (Youth Fair)

July belongs to the youth of Greene County. The Greene County Fair showcases the talent and creativity produced through 4-H Club participation. Along with its agricultural grandeur, this fair also provides other means of entertainment for all ages. Children can enjoy the activities area, while the adults can partake in the traditional forestry and conservation displays.


August 3 – 8: Ulster County Fair

A pay-one-price ticket gives you access to more than 20 fair rides for all ages, exhibits from the county sheriff’s office and local 4H, and headlining shows, from Sass and Brass to Emily Ann Roberts. Don’t forget to indulge in a generous helping of fried Oreos or funnel cake before you watch the nighttime fireworks.

New Paltz;

August 24 – 29: Dutchess County Fair

For its 175th year, New York State’s second largest county fair returns to Rhinebeck. Spend a day at its one-of-a-kind mix of gardens, agricultural exhibits, and Century Museum Village with in-costume storytellers. Plus, explore traditional fair activities, like hitting the wild. adrenaline-inducing rides and trying every type of carnival food you could imagine, for a truly memorable way to end the summer.


September 1 – 6: Columbia County Fair

The Columbia County Fair returns for its 181st year, bringing back midway rides, monster tractors, livestock, crafts, talent competitions, a firefighters’ parade, and more.



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