Best of Hudson Valley: Fun and Leisure in 2024

Kick back, relax, and have a blast with help from these Best of Hudson Valley winners in the fun and leisure category.

-Editor Pick-

Fire Tower Hike

Overlook Mountain, Woodstock

The Hudson Valley has more than a dozen fire towers—but how many have hotel ruins and pretty panoramas from rockfaces? Overlook Mountain is perfect from spring to fall (emphasis on the latter, since it boasts some of the best leaf-peeping in the Valley) and can double as a starting point for a Woodstock day trip.

Overlook Mountain, Woodstock
Photo by Francesca Furey

-Reader Picks-

Annual Festival

NYS Sheep and Wool Festival, Rhinebeck


District Social, Beacon

- Advertisement -

Arts and Crafts Fair

Rhinebeck Crafts Festival, Rhinebeck

Bed & Breakfast

Watergrasshill Bed & Breakfast, New Paltz

Bike Trail

William R. Steinhaus Dutchess Rail Trail

Boutique Hotel

Hudson Whaler, Hudson

Bowling Alley

Spins Bowl, multiple locations

- Partner Content -


Yogi Bear’s Jellystone Park Camp-Resort, Gardiner

Christmas Attraction

ERDAJT Christmas Light Display, Lagrangeville

Comedy Club

Laugh it Up Comedy Club at Mahoney’s Irish Pub, Poughkeepsie

County Fair

Dutchess County Fair, Rhinebeck

- Advertisement -

Dance Club

Silk Factory, Newburgh

Drag Show

Yas Diva @ The Roosevelt Bar, Beacon

Drive-In Theater

Overlook Drive-In Theatre, Poughkeepsie

Food Festival

Hudson Valley Garlic Festival, Saugerties

Golf Course

The Links at Union Vale, Lagrangeville

Golf Course

Beekman Golf Course, Hopewell Junction

Halloween Attraction

Headless Horseman Hayrides and Haunted Attractions, Ulster Park

Historic Site

Vanderbilt Mansion, Hyde Park

Horseback Riding Stable/Ranch

Rocking Horse Ranch, Highland


Mohonk Mountain House, New Paltz

Reader Pick: Mohonk Mountain House, New Paltz
Reader Pick: Mohonk Mountain House, New Paltz. Photo courtesy of Mohonk Mountain House.

Hudson River Cruise

Hudson River Cruises, Kingston

Ice Skating Rink

Bear Mountain Ice Rink, Tomkins Cove

Indoor Music Venue

The Bardavon, Poughkeepsie

Jazz Club

The Falcon, Marlboro


The Karaoke Boys, Beacon

Kayak or Paddlesport Rental

Hudson River Expeditions, multiple locations


Walkway Over the Hudson, Poughkeepsie

Mini Golf

Kelly’s Creamery Mini Golf, Dover Plains

Movie Theater

Roosevelt Theatre, Hyde Park


Franklin D. Roosevelt Library and Museum, Hyde Park

Music Festival

Hudson Valley Jazz Festival, multiple locations

Neighborhood/City to Explore


Outdoor Music Venue

Bethel Woods Center for the Arts, Bethel

Pick-Your-Own Farm

Fishkill Farms, Hopewell Junction

Reader Pick: Fishkill Farms, Hopewell Junction
Reader Pick: Fishkill Farms, Hopewell Junction. Photo by Grant Delin.

Picnic Spot

Bear Mountain State Park, Tomkins Cove

Place to Go Apple Picking

Dubois Farms, Highland


View this post on Instagram


A post shared by DuBois Farms (@duboisfarms)

Place to Take Out-of-Towners/Visitors

Walkway Over the Hudson, Poughkeepsie

Pumpkin Patch

Dykeman Farm, Pawling


Mohonk Mountain House, New Paltz

Rollerskating Rink

Hyde Park Roller Magic, Hyde Park

Sculpture Garden

Storm King Art Center, New Windsor

Reader Pick: Storm King Art Center, New Windsor
Reader Pick: Storm King Art Center, New Windsor. Photo by Jerry L. Thompson.

Sip and Paint

Board and Brush, Wappingers Falls

Ski Resort

Hunter Mountain, Hunter

Trivia Night

Publick House 23, Pleasant Valley

Walking/Hiking Trails

William R. Steinhaus Dutchess Rail Trail, Dutchess County


SplashDown Beach Water Park, Fishkill


Catamount Zip Tour, Hillsdale

Catamount Zip Tour, Hillsdale
Reader Pick: Catamount Zip Tour, Hillsdale. Photo courtesy of Catamount Zip Tour.

Related: Here’s What to Do in the Hudson Valley This Week

Our Digital Partners

Learn how to become a digital partner ...

Our Excellence in Nursing Awards take place on May 1!

Our Best of Hudson Valley ballot is open through March 31!

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.