Where to Go on a Summer Date in the Hudson Valley

From farmers' markets to drive-in movies, here's where to go on a fun and memorable date with your significant other this summer.

Queue up the “summer summer summertime, ooh summertime,” DJ Jazzy Jeff & The Fresh Prince song while heading to some of these fun spots with your significant other this summer for date night (or day, because afternoon dates are a thing, too). Whether you’re looking to stay cool at a spa or spend time outdoors exploring or watching movies, there’s something for every Hudson Valley couple!

Albany County

Above All Balloon Rides


summer date
Photo courtesy of Above All Balloon Rides.

If you are an adventure-loving couple, start the summer on a high note with a hot air balloon ride with Above All Balloon Rides! See a 360-degree view of the beautiful Hudson Valley including the Catskills, Berkshires, and even Adirondacks with your person. This bucket-list activity can be perfect for an anniversary date celebration, engagement, or any other special occasion. Choose from picturesque sunrise or sunset rides. Book a private two-person balloon for $500 per person, or share a balloon with six to seven people for $300 per person. The experience takes about three to four hours and includes balloon inflations, flight time, landing and pack up, as well a post-flight beverage cheers. You’re in safe hands with Above All Balloon Rides as all balloons are checked and FAA certified and regulated. Scott Griswold, balloon pilot and owner of Above All Balloon Rides, has been flying for over 30 years. Click here to book.

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summer date
Photo courtesy of Above All Balloon Rides.

Columbia County

Art Omi

Ghent, 518.392.4747


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Attention art-loving couples—experiencing Art Omi is a must! This summer, get lost with your lover at this outdoor sculpture garden, and bring your pup if you have one for a fun adventure outside. Be sure to stop by the cafe for treats, then take them to go for a little picnic. You may have seen Olaf Breuning: Clouds on Instagram, and seeing it in person is worth the trip. This summer, check out music, dance, open studio events and more; see the full lineup of happenings here.

Dutchess County

Four Brothers Drive-in

Amenia, 845.373.8178

Photo Courtesy of Four Brothers Drive In.

There’s just something special about a drive-in movie theater, especially when it’s a cool summer night. This drive-in movie theater looks straight out of an indie rom-com! Four Brothers Drive-In is open seven days a week and has double features playing. The food selection goes beyond the standard moviegoing fare; it includes lobster rolls and margaritas! If that doesn’t sound perfect enough, check out the onsite accommodations, where you can stay in a quaint Airstream. For more information on how to book Hotel Caravana, click here.

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Elk Ravine Farm

Amenia, 914.262.4737

Before you head over to see a drive-in movie showing, go on a tour and enjoy the beautiful Scottish Highland cattle at Elk Ravine Farm. After all, what’s cuter and more romantic than fluffy Scottish Highland calves? Elk Ravine Farm’s two-hour private tours are seven days a week at 10 a.m., 12:30 p.m., and 3 p.m., as well as seasonally at 5:30 p.m., daylight permitting. Click here to book a tour.

Greene County

Wylder Windham


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Rest, relax, repeat. Unwind and relax with a cold drink in hand at Wylder Windham for a wonderful spa weekend with your significant other. The resort’s list of summer events during the weekend includes activities like cocktail making, s’mores, cookie decorating, and more fun events that are perfect for date night.

Orange County

Pennings Farm Cidery

Warwick, 845.987.9922

Sip on delicious apple cider drinks and enjoy al fresco dining at Pennings Farm Cidery in Warwick. Lounge on the lawn and listen to Hudson Valley musicians at their live music summer sessions happening from June to late July. Click here to see the lineup. P.S. Check out Pennings’ brick-oven pizza and cider tastings for an added bonus during your summer date experience.

Putnam County

Sometimes a day trip is just what you need for a perfect summer date. There’s something magical about wandering through the local shops and stopping in for a sweet treat here and there. First, head over to Stonecrop Gardens, a magical garden filled with flowers and beautiful displays. Then, get lost in the dozens of local shops including bookstores, boutiques, and clothing joints. Top off the trip with a sweet treat at Moo Moo’s Creamery, a fan-favorite ice cream shop in the region.

Stonecrop Gardens

Cold Spring, 845.265.2000


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Take in the picture-perfect gardens filled with many beautiful blooms. Stonecrop Gardens is open on Monday, Wednesday, Friday, and Saturday, as well as one Sunday per month with tea and cake available for purchase. Register on the website for Saturday and Sunday visits.

Moo Moo’s Creamery

Cold Spring, 845.204.9230


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During the summer, Moo Moo’s Creamery stays open a bit later than usual. It makes fresh handcrafted ice cream and has rotating flavors each day. Choose from one, two, or three scoops, or pick up a pint to take home with you.

Rensselaer County

Troy Waterfront Farmers Market

Monument Square, Troy
Saturdays, 9 a.m. – 2 p.m.

Pick up local produce, goodies, and flowers for the perfect picnic at Troy Waterfront Farmers Market this summer. Stroll through the booths of the makers and vendors at the market on Saturdays from 9 a.m. to 2 p.m. This summer market is a staple in the community and has been running for nearly 25 years. Once you have your favorites, head a few blocks down to William D. Chamberlain Riverfront Park. Snap a photo and add it to your summer photo album.

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

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