4 Things to Do in Windham, NY
for Couples


Looking for romantic things to do for a long weekend trip in Windham, NY? Nestled at the base of the picturesque Catskills Mountains, and offering bountiful opportunities for outdoor activities, Windham is the perfect weekend destination for those looking to reconnect with nature.

From rugged hiking on The Windham Path to hitting snow-covered slopes at Windham Ski Resort, and horseback riding at Mountain Brook Farm, outdoor lovers will never run out of exciting things to do in the area.

Here’s four of our top recommendations of things to do for couples who don’t mind roughin’ it and getting some direct underneath their nails.

1. Ski Windham Mountain, NY

Get your adrenaline pumping with a day spent exploring powdered slopes at the stunning Windham Mountain Ski Resort, just two hours from New York City. Offering over one thousand five hundred feet of vertical gain and fifty-four groomed trails alone, you’ll find plenty of routes to test your skills and private ski instruction to improve your physical and mental game.

Looking to take your thrill to the next level? Take a lift up to six terrain parks, reeling in over eighty features to practice freestyle skiing to your heart’s content. Seasonal Ikon and Day Passes are accepted.

Insider Tip: Be sure to stop by the resort’s restaurant, Tavern 23, for delicious and zesty Thai Chili Wings.

Ski Windham Mountain

2. Explore the Windham Path

Looking for the perfect hike in Windham? Located just minutes from the heart of town, the Windham Path is a local’s favorite for walking and biking with expansive views of the rolling Catskills Mountains.

Offering over two miles of paved pathway, you’ll cross charming wooden bridges over the famed Batavia River, explore secluded wooded areas, and journey through open meadows blazing with wildflowers in the Spring.

Open all four seasons, you can even snowshoe this path to get in the holiday spirit when it becomes a winter wonderland!

Insider Tip:  Guests at Wylder Windham Resort get complimentary mountain and e-bike cruisers during their stay.

Discover The Windham Path

3. Horseback Riding at Bailiwick Animal Park & Riding Stables

Ready to see the Catskill Mountains from a different point of view? Operating since 1963, this family-owned ranch will blow your mind with 300+ private acres nestled at the foot of the Catskill Mountains. The Riding Stable is still in operation today and offers guided mountain tours daily. The stables are home to over 50 horses and ponies.

Both private and group lessons are available for all ages and abilities. Show your room key to receive 10% off of your lesson.

Insider Tip: Make sure to stop by their park to view over 40 exhibits of domestic & exotic animals!

4. Visit The Vineyard at Windham

Who says you can’t sum up an adventurous mountain day with some wine tasting? Spanning four acres, The Vineyard at Windham is a magical place to discover your new favorite wine, house-produced, plus top-rated locally-produced bottles, and a stunning outdoor patio to take in the views in the warmer months. 

Insider Tip: The Vineyard is reservation only, and slots are opened on a sixty-day rolling basis.

Explore The Vineyard at Windham

Romantic Stays in the Heart of Windham

Located just a stone’s throw from the Windham Mountain ski area, wine tasting at The Vineyard, and The Windham Path, Wylder Resort is an upscale, yet rustic mountainside resort, perfect for your romantic getaway.

Explore Romantic Stays