The Best Activities for a Summer Trip to Woodstock, NY
Summer is prime time in Woodstock, New York. Long sunny days, lush green mountain foliage, and a bustling town square make the Catskills the ultimate summer destination. Whether you’re cooling off in a swimming hole, spending an evening listening to live outdoor music, or exploring local farm stands, summer in Woodstock offers an unforgettable mountain escape. Located just two hours north of New York City, it’s the perfect summer retreat. Here are the best things to do in Woodstock during the summer months.
Cool Off in Local Waters & Swimming Holes
When the summer heat hits, there’s nothing better than dipping into the cool mountain waters around Woodstock:
Ottine’s & Local Creeks: The Sawkill Creek runs right through town, offering scenic spots to wade or relax by the water.
Big Deep & Little Deep: Historic local swimming holes tucked into the woods near town, perfect for a quick, refreshing dip on a hot afternoon.
Ashokan Reservoir: While swimming isn’t permitted in the reservoir itself, walking or biking along the paved Ashokan Rail Trail offers cooling mountain breezes and incredible panoramic water views.
Hike to Panoramic Mountain Views
Summer foliage turns the Catskills into a dense, vibrant green paradise.
Overlook Mountain: A summer favorite. The shaded trail leads up to the historic hotel ruins and the fire tower, offering breathtaking views of the Hudson Valley and the Ashokan Reservoir.
Onteora Lake Trail: Ideal for a lighter summer walk through cool hemlock groves and along quiet lake shores.
Tip: Summer weekends can get busy at popular trailheads. Plan to arrive early in the morning to secure parking and beat the midday heat.
Experience Outdoor Music & Summer Festivals
Music is in Woodstock's DNA, and summer brings the scene outdoors:
The Colony: The expansive back yard and beer garden at The Colony host outdoor summer concerts, lawn games, and open-air dining under the stars.
Bearsville Theater: Check their summer schedule for outdoor deck events, festivals, and evening shows along the creek.
Woodstock Playhouse: Located at the entrance to town, the landmark playhouse hosts summer theater productions, dance performances, and musical events throughout the season.
Explore Flea Markets, Farm Stands & Town Life
Summer in town is buzzing with activity.
Mower’s Flea Market: Running every Saturday and Sunday throughout the summer, this open-air market behind Bread Alone is packed with vintage finds, handmade jewelry, local produce, and art.
Farm Stands & Pick-Your-Own: Take a short drive to nearby farms like Blue Mountain Bistro-to-Go for gourmet picnic supplies, or head to local orchards and berry patches in the Hudson Valley for summer fruit picking.
Tinker Street Strolls: Spend late afternoons wandering through local art galleries, ice cream shops, and unique boutiques.
Dine Al Fresco
Summer evenings in Woodstock are meant for outdoor dining. From the garden patio at Cucina to the creek-side seating at Bearsville, enjoying a meal outdoors is a must. Because summer is the peak tourist season in the Catskills, we strongly recommend making dinner reservations a few weeks in advance for popular spots like Sylvia, Good Night, or Cucina.
Relax and Enjoy the Mountain Air
Despite the summer energy, Woodstock remains a sanctuary for relaxation. Spend a lazy afternoon reading in a hammock, enjoying a cold drink on the patio, or taking a sunset drive along Route 28 and Route 214 as dusk settles over the peaks.
Summer is an incredible time to experience everything Woodstock and the Catskills have to offer. From hiking and swimming to live music and outdoor dining, there’s no shortage of adventure. Because summer is peak season, be sure to plan your trip and book your accommodations early!