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Plan Your Ultimate Pre-Summer Weekend at 8 Hudson Valley Events




Westchester Magazine Event: Wine & Food Festival

Various locations in Westchester
June 4-9

Beginning on Tuesday, our sister publication Westchester Magazine kicks off its annual weeklong celebration of Westchester County’s thriving culinary scene. If you’ve never been to the epic food fest before, expect only the best eats and drinks from the region’s premier chefs and restaurants.

The party starts on Tuesday with the Salute! Wine Tasting Tour of Italy featuring vino extraordinaire Kevin Zraly. On Wednesday, fashionistas flock to The Westchester for Taste & Style, a shopping and dining shindig. Then on Thursday, burger lovers get their hands dirty at the all-inclusive Burger & Beer Blast at Kensico Dam Plaza. The following day, Westchester Magazine debuts its first-ever Food Truck Festival in Yonkers and its one-of-a-kind Winemakers Dinner at four top-tier local eateries.

Of course, we can’t forget about the most delectable event of them all! On Saturday, from 12-4 p.m., the Grand Tasting Village brings more than 50 restaurants and 200 wines and spirits to Kensico Dam Plaza for a wining and dining fest unlike any you’ve been to before. The party comes to a close on Sunday with the Jr. Chef Experience, a special event just for the budding chefs in your life.



Innovation Challenge

Locust Grove, Poughkeepsie
June 5, 4:30-7 p.m.

Returning for its second year, the Think Dutchess Alliance for Business Innovation Challenge spotlights the brightest creators in the region to help them take their innovative ideas to the next level. At this week’s event, four semi-finalists face off in a live pitch competition to convince the audience that they have what it takes to succeed as entrepreneurs.

In 2019, semi-finalists run the gamut from a 3D manufacturing company and a food-centric social enterprise to cutting-edge handicap technology designer and an aviation innovation group. Want to know who will come out on top? Purchase tickets for $40, then enjoy dinner and drinks as you learn about the brands and their aspirations in the Hudson Valley.


Park and Play Movie Night

Samaritan Hospital – St. Mary’s Campus, Troy
June 7, 7:30-10 p.m.

Need something to do with the kids this weekend? Bring them to Troy’s free Park and Play Movie Night on Friday. After the school and work day wraps up, families can head to the hospital campus to catch a screening of The Greatest Showman, the Academy Award-nominated flick starring Hugh Jackman as ringleader P.T. Barnum.

Blankets and lawn chairs are ok to bring, but make sure to get there early to take advantage of free parking at St. Mary’s, since spaces may fill up by the time the opening credits flicker onto the screen.


Brewster Music Festival

Wells Park, Brewster
June 8, 12-7 p.m.

Love local music but not the ticket price attached to it? Keep summer fun costs down by checking out Brewster’s free festival on Saturday. Held at the scenic Wells Park, the event brings area bands like Special Sauce, Fishkill George & TFM, and The Libertine Project, to name only a few, to the grounds.

Pack your own chairs and blankets to set up shop on the great lawn, then kick back with good tunes and great bites from local vendors. It’s going to be a beautiful day!




Bethel Woods Center for the Arts, Bethel
June 8, 6 p.m.

The summer’s hottest pop music concert returns to the Hudson Valley on Saturday. Held at Bethel Woods, K104.7’s KFEST brings some of the hottest names in the music industry to the historic venue for an evening of back-to-back performances.

Headliners in 2019 are Ciara and Shaggy, along with Bazzi, Bryce Vine, Fletcher, Jake Miller, and Jeremy Zucker. If you want to grab last-minute lawn tickets, pick them up now for $28 — a steal in our book!


WOLF + LAMB’S Catskills Roller Disco

Skate Time 209, Accord
June 8, 8:30 p.m. – 12 a.m.

Break out the leg warmers and embrace all the hair spray for Wolf + Lamb’s retro roller disco on Saturday night. Bound to be a party like no other, the event mixes throwback tunes with the funkiest fashions of the 70s and 80s. Get your tickets in advance if you want to go, since they’re $20 pre-sale or $25 at the door, then test your skating skills in the Roller Relay, Freeze Tag, or Limbo competitions. If you’re just there for the vibes, Skate Time 209 has you covered with refreshing sips in the beer garden.


Wizard of Oz

Photo provided by New York Academy of Ballet


The Wonderful Wizard of Oz

Bardavon, Poughkeepsie
June 8, 2 and 6:30 p.m.

You don’t have to go all the way to Kansas to find the yellow brick road this week. Thanks to the Poughkeepsie City Ballet, the fantastical tale of one girl and her incredible adventure takes the stage at the Hudson Valley’s historic Bardavon Opera House. During the show, which occurs twice during the day at 2 p.m. and 6:30 p.m., students from the New York Academy of Ballet join the colorful cast to bring to life the world that Frank Baum created more than 100 years ago. Tickets cost $15 for adults and $12 for students, seniors, and children 12 and under.


Rob Richards in Concert

Davis Chapel, New York Military Academy, Cornwall-on-Hudson
June 9, 2 p.m.

For a real family fun treat, pick up tickets to see organist Rob Richards in concert at the New York Military Academy on Sunday. As the house organist at Disney’s El Capitan Theatre in Hollywood, Richards brings fairytale tunes and iconic songs to the Hudson Valley during one very special afternoon event. As if that isn’t exciting enough, the show also marks the first performance at the Academy in over a decade. 


Elsewhere in the Hudson Valley this weekend, Disc Jam spins bass tunes in Stephentown while Taste of Country rocks Hunter Mountain. Local pride festivities continue, bringing a rainbow of color to Poughkeepsie and Albany. For foodies in the area, Farm to Fork Fondo delivers a fitness twist to the culinary scene in Warwick.

Over in Stormville, the airport’s Food Truck & Craft Beer Festival shines a light on the region’s coolest traveling eats and drinks (we’re talking 15-plus trucks and more than 50 craft beers and ciders). Last but not least, for nature lovers, Kingston’s Kayak Festival gets everyone ready for rowing season along the Hudson River on June 8.

Related: An Insider’s Guide to June Events in the Hudson Valley

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