Best of Hudson Valley: Fun and Leisure in 2023

These Best of Hudson Valley businesses and destinations offer everyone the chance to kick back, relax, and have a blast.

Annual Outdoor Event

New York Renaissance Faire, Tuxedo


District Social, Beacon

Arts and Crafts Fair

Rhinebeck Arts & Crafts Fair

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Bed & Breakfast

The Bird & Bottle Inn, Garrison

Bowling Alley

Spins Bowl, Poughkeepsie

Christmas Attraction

ERDAJT’s Christmas Light Display, Lagrangeville

Comedy Club

Laugh It Up, Poughkeepsie

County Fair

Dutchess County Fair, Rhinebeck

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Drag Show

Sunday Drag Brunch at Mama Roux, Newburgh

Drive-In Theater

Warwick Drive-In Theater, Warwick

Food Festival

Garlic Festival, Saugerties

Golf Course (Private)

West Hills Country Club, Middletown

Halloween Attraction

Headless Horseman, Ulster Park

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Horseback Riding Stable/Ranch

Rocking Horse Ranch, Highland


The Thayer Hotel at West Point, West Point

Hudson River Cruise

Hudson River Cruises, Kingston

Ice Skating Rink

Bear Mountain Ice Rink, Tompkins Cove

Indoor Music Venue

Daryl’s Club House, Pawling

Jazz Club

The Falcon, Marlboro


Mahoney’s Irish Pub & Steakhouse, Poughkeepsie

Kayak or Paddlesport Rental

Hudson River Expeditions, Cold Spring


Walkway Over the Hudson, Poughkeepsie

Mini Golf

DC Sports, Wappingers Falls

Movie Theater

Roosevelt Theaters, Hyde Park


Dia Beacon

Music Festival

Hudson Valley Jazz Fest, multiple locations

Neighborhood/City to Explore


Outdoor Music Venue

Bethel Woods Center for the Arts, Bethel

Picnic Spot

Vanderbilt Mansion, Hyde Park

Pop-Up Market

Stormville Airport Antique Show and Flea Market


Mohonk Mountain House, New Paltz

Rollerskating Rink

Hyde Park Roller Magic, Hyde Park

Sculpture Garden

Storm King Art Center, New Windsor

Sip and Paint

Pinot’s Palette, Fishkill

Trivia Night

Juan Murphy’s, Poughkeepsie

Walking/Hiking Trail

Lake Minnewaska Loop, Minnewaska State Park

Arts and Crafts Fair
Mike Lawrie Photography

-Editor’s Pick-

Biannual Arts and Crafts Fair

Woodstock–New Paltz Art & Crafts Fair, Ulster County Fairgrounds

With dozens of makers showing off beautiful handmade clothing, furniture, jewelry, and home décor, this fair has something for everyone—seriously, you won’t leave empty-handed. Food vendors, live entertainment, and a craft tent for kids make this an all-day event.

Bike Trail
Adobe Stock/ stockphoto-graf

-Reader’s Pick-

Bike Trail

Dutchess Rail Trail

Cycle 13 miles of hamlets and towns like Hopewell Junction, East Fishkill, Wappinger, LaGrange, and Poughkeepsie. The paved path is a part of the 750-mile Empire State Trail and traverses along an abandoned railroad. The picturesque route eventually connects to the Walkway Over the Hudson, with stunning river views.

Courtesy of Splashdown Beach

-Reader’s Pick-


SplashDown Beach, Fishkill

Dive into “America’s biggest little waterpark” where kids go nuts for 14 thrilling attractions. From Cowabunga Falls and Croc Creek Wavy Lazy River to the Arctic Mammoth and the Pirate Plunge, guests are sure to smile and get their fill of aquatic fun.

cooking classes
Adobe Stock/ Alenkadr

-Reader’s Pick-

Cooking Class

The Culinary Institute of America, Hyde Park

What better place to polish your cooking skills than at this world-renowned culinary school? The CIA’s public offerings range from courses in basic cooking and plating techniques to intensive workshops for international cuisines—like Mediterranean or Hawaiian. If you see a class that interests you, book early—spots go fast.

gold course
Adobe Stock/ Dave Willman

-Reader’s Pick-

Golf Course (Public)

Winding Hills Golf Club, Montgomery

Set in rural Orange County, this lightly challenging, 18-hole public course is surrounded by beautiful forests and rolling slopes. Modeled after famous course designer Geoffrey Cornish’s award-winning Blue Rock on Cape Cod, you can play like a pro close to home.

Related: Where to Go and What to Bring for a Perfect Picnic in the Hudson Valley

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