Explore Westchester’s collection of thematic trails that highlight the region’s culture, history and craft. Walk in the footsteps of patriots along the American Revolutionary Trail, with highlights like the Jacob Purdy House, Thomas Paine’s Cottage, Saint Paul’s Church, Philipsburg Manor and the John Jay Homestead. Discover powerful stories of resilience on the African American Heritage Trail, which features landmark sites celebrating the cultural and civic contributions of Black individuals. And for a flavorful detour, raise a glass along the Westchester Craft Beverage Trail – a self-guided tasting tour of standout breweries, cideries and distilleries across the County.
For hikers and outdoor enthusiasts alike, Teatown Lake Reservation (Ossining) has nearly 15 miles of trails open annually from dawn until dusk and also offers the community a space to learn about local wildlife. Trails – varied in level of difficulty – offer views of diverse terrain, habitats, lakes, swamps and more. Don’t miss special programming like “Snow Stories” and the “Full Moon Hike” series.
Spread your wings at Teatown’s 21st Annual Hudson River EagleFest® on Feb. 7, 2026, held at Croton Point Park (Croton-on-Hudson). Celebrate winter’s coolest visitors with live bird shows, guided eagle-spotting walks, heated tents, kids' crafts, games, food trucks and more. Arrive in style aboard the Metro-North Railroad Eagle Train departing at 9:25 a.m. from Grand Central Terminal and 8:58 a.m. from Poughkeepsie. Each departure features a dedicated train car with a guest naturalist aboard.
Adventurous travelers can throw on their warmest gear and head to one of Westchester’s trails, ideal for cross-country skiing and snowshoeing. One prime spot is Croton-on-Hudson’s Croton Point Park, with 508 acres on a peninsula situated alongside the Hudson River. The Kitchawan Preserve, a 208-acre natural preserve along Route 134 (Ossining), is a cross-country skier’s paradise, with the North County Trailway running across its eastern border. Cranberry Lake Preserve (White Plains) is also a great choice, while Ward Pound Ridge Reservation is the County’s largest park with well-maintained trails and varied terrain.
Tap into winter fun when maple sugaring season returns to Westchester in 2026. From January through March, Enjoy family-friendly events featuring hands-on tree tapping, maple tastings and educational demonstrations that highlight the sweet science behind syrup making. Events include Maple Saturday at Lenoir Preserve (Yonkers) on Mar. 7, Teatown's Pancake Brunch(Ossining) on Mar. 15, Sugaring Off Party at Ward Pound Ridge Reservation (Pound Ridge) on Mar. 21. Conclude the maple celebrations at New York State's Maple Weekend, Mar. 21-22 and 28-29, with a hearty pancake breakfast at Yorktown Grange followed by sugaring demonstrations, trail walks, tours and tastings at White Oak Farm (Yorktown).
Indoor Activities
Catch the ringside excitement at the International Sumo League's World Championship Sumo (WCS) event on Jan. 30 at the Westchester County Center. Cheer on 12 of the world’s top professional sumo wrestlers as they compete in 30-40 matches to crown a WCS champion.
For days when the indoors beckon, visitors can embrace their artistic side at The Pottery Factory (Mount Kisco), which offers an instructor-led paint and sip party session.
Golfers should visit the newly opened Five Iron Golf (Port Chester). Outfitted with state-of-the-art Trackman technology and high-speed cameras, visitors can use the simulator to choose their own adventure: tee it up at champion-level courses or challenge each other in one of the games. There’s something for every level of golfer.
Warm up inside at Bowlero (White Plains), which offers endless fun for all ages with 56 bowling lanes, an arcade with old-school classics like Mario Kart or Pac-Man, and a sports bar.
Explore Westchester’s vibrant museum scene this winter. The Hudson River Museum (Yonkers) blends art, history and science with over a century of cultural richness. The Hammond Museum & Japanese Stroll Garden (North Salem) offers a peaceful blend of Eastern and Western influences, featuring a bamboo grove, waterfall and koi-filled ponds. Hudson Valley MOCA (Peekskill) rounds out the experience with cutting-edge contemporary works from global artists.
Beginning Jan. 9, Signature Tours of the historic Rosen House will be offered at Caramoor (Katonah) on Fridays and Saturdays. Step inside the Mediterranean-style villa on these docent led tours to behold art and furnishings from the Renaissance, Chinese art and entire rooms styled from the great houses of Western Europe.
Families will find hours of entertainment for the kids at LEGOLAND Discovery Center Westchester (Yonkers), the ultimate indoor LEGO® playground with endless building adventures and interactive experiences.
Let kids’ imaginations soar at the Westchester Children’s Museum (Rye). This hands-on learning space invites children to design, create and discover together. With interactive exhibits and creative exploration at every turn, it’s a place where curiosity is encouraged and learning feels like play.
For those looking for a moment of relaxation, visit Oasis Day Spa (Dobbs Ferry) to enjoy seasonal services like the Collagen Facial with Microcurrent for a lifted, glowing complexion and the Autumn Sports Trio Massage, featuring Arnica aromatherapy and Vital Body CBD cream to ease tension and prepare for winter wellness.
Valentine's Day Festivities
Westchester has plenty of ways to spend some time with those you love on Valentine’s Day. Through Feb. 14, reserve a Winter Igloo for up to 10 people at The Sailhouse restaurant for a cozy winter experience featuring stunning Hudson River views and seasonal bites and cocktails.
Looking to spend some time outdoors? Venture out Feb. 14-15 to Wolf Conservation Center and howl along with the pack while making special wolf valentines. Adults can learn about breeding wolf pairs on Feb. 7 & 14 at the Mating & Dating program, complete with wine and snacks.
For movie buffs, catch a flick at Jacob Burns Film Center Feb. 13-15 and enjoy special savings on Prosecco at the Take 3 Wine Bar & Café.
Seasonal Bites & Drinks
1730 Wine Bar (Mount Vernon) which offers a variety of popular and specialty wines for an international vibe representing local and regional favorites. This cozy wine bar also offers a full menu of creative dishes, comfort foods and brunch options.
Resolutions in the new year often call for healthy meals. From protein to nutrient-rich veggies and leafy greens, there are plenty of health-conscious options in the area. Try Root 2 Rise (Pleasantville), which makes each dish from scratch using organic, locally sourced, whole ingredients free of refined sugars, preservatives and seed oils. Grass Roots Kitchen (Tarrytown) offers local and seasonal plant-based favorites as well.
Nothing says perfect winter date night like a creative, cozy cocktail. Try the Whistling Rail (Bronxville) for a romantic evening of speakeasy vibes, tapas and some live jazz music.
At The Blind Pig of Westchester (White Plains), a 1930s-themed cocktail bar, don’t miss the Irish coffee – it’s a warm, whiskey-strong, slightly sweet, frothy, cream-topped caffeine boost.
Make a stop along the Westchester Craft Beverage Trail at Hardscrabble Cider (North Salem) to try their mulled cider — from apples grown on the premises — mixed with bourbon made by The Spirits Lab in Newburgh, including pure maple syrup, lemon juice and bitters. The Craft Beverage Trail showcases the region’s thriving craft beverage scene, featuring a variety of options from distilleries to craft breweries, a cidery and even a micro winery.
Find a caffeine fix to warm up on a cold winter’s day at Horsefeathers (Tarrytown) by choosing from one of their spiked coffees including Irish (with Irish whiskey), Mexican (Kahlua), Captains (Captain Morgan), Brotherhood (Frangelico), Cafe di Roma (sambuca), Cafe Almondine (amaretto), and Bailey’s Mocha (Bailey’s and chocolate).
Where to Stay
Tucked along a peaceful, tree-lined road, the Kittle House Inn (Chappaqua), formerly known as Crabtree’s Kittle House Restaurant & Inn, has plans to reopen guestrooms in early 2026, offering a luxurious escape that combines the elegance of Old New York with historic charm. The restaurant reopened on Nov. 19, 2025, giving visitors a head start in experiencing the property’s fine dining, celebrated wine offerings and exceptional hospitality.
The Bedford Post Inn (Bedford) is a quaint historic property dating back to the 1860s that will transport visitors to a scene from their favorite Hallmark holiday movie. It’s been restored and is home to an eight-room luxury inn, a yoga studio and two distinct restaurants. Cozy interiors are perfect for ignoring winter’s chill, including amenities such as heated bathroom floors and freestanding soaking tubs, offering a serene retreat for guests to unwind.
The Royal Regency Hotel (Yonkers) offers stylish rooms and modern amenities, providing a comfortable and upscale experience just minutes from New York. Enjoy a relaxing Date Night-In package with champagne, chocolate truffles and a $50 in-room dining certificate.
The luxurious Tarrytown House Estate’s Cozy Couples Getaway package includes chocolates, sparkling wine and late check out.
