Windham, NY
Places to visit in Windham, NY
Eastwind Windham
Nestled in the heart of the Catskills, Eastwind Windham offers a serene escape from the hustle and bustle of city life. This boutique hotel is renowned for its Scandinavian-inspired design, seamlessly blending rustic charm with modern amenities. Guests can unwind in thoughtfully curated rooms or cozy up in one of the private Lushna cabins, boasting panoramic views of the lush mountain landscape.
Eastwind Windham is more than just a place to stay; it's a gateway to adventure. Explore nearby hiking trails, enjoy skiing in the winter, or simply relax in the sauna and soak in the peaceful surroundings. With its on-site bar and lounge, offering curated cocktails and local brews, Eastwind invites you to savor the flavors of the Hudson Valley. Whether you're seeking solitude or a romantic getaway, Eastwind Windham promises a memorable retreat in one of New York's most picturesque regions.
Gardenheir Windham
Gardenheir is a beautifully curated garden-inspired lifestyle shop nestled in Windham, NY—a surprising but fitting home for a boutique that blends horticulture, design, and fashion. Founded by partners Alan Calpe and Christopher Crawford, Gardenheir grew from their personal journey into gardening after relocating from New York City to the Catskills. What began as a pandemic-era passion project evolved into a nationally recognized brand known for its distinctive blend of heritage garden tools, thoughtfully designed apparel, and whimsical-yet-practical accessories. Their signature Italian-made clogs and stylish garden smocks have become cult favorites among green thumbs and design lovers alike.
Stepping into the Windham store is like walking into a gardener’s dream—rows of museum-worthy spades, artisan-made hand creams, bespoke collaborations with legacy brands like Haws and Sneeboer, and a warm, personal atmosphere. Gardenheir’s aesthetic bridges high style and humble soil, offering everything from vintage garden antiques to sustainably sourced tools. Beyond retail, it's a space of community and discovery, where passionate gardeners and creative spirits gather to exchange tips, stories, and inspiration. With growing demand and an ever-evolving product line, Gardenheir is not just a shop—it’s a cultural moment in the making for a new generation of modern stewards of the land.
Hayfield Catskills
Nestled in a breathtaking valley framed by the Catskill Mountains, Hayfield Catskills is a wedding venue where natural beauty and timeless craftsmanship meet. Two centuries-old barns, lovingly restored to preserve their hand-hewn beams, tin roofs, and century-old magic, sit at the heart of this extraordinary property. As sunlight filters through the rafters and fireflies emerge after twilight, Hayfield feels both enchanted and deeply grounded. With panoramic mountain views, candy-colored sunsets, and nights illuminated by the Milky Way, it’s a setting that feels as if it were designed for love stories to unfold.
Each barn at Hayfield seamlessly blends rustic character with modern refinement. Thoughtfully appointed with pristine hardwood floors, antique hand-blown-glass lighting, new bathrooms, and full amenities, the space can host intimate gatherings or elegant formal affairs. Outdoor ceremonies take place on the grassy knoll with sweeping views of the valley, while receptions transition into the barns for dining and dancing beneath soaring 35-foot ceilings. Handcrafted wooden tables and benches built locally using traditional joinery bring a sense of artistry and authenticity to every celebration, while vintage furnishings and a century-old bar complete the venue’s one-of-a-kind atmosphere.
What truly sets Hayfield apart, however, is its intimate approach. Hosting only a dozen events each season from May through October, the team provides personalized support throughout the planning journey, from curating vendor recommendations to coordinating design details. Surrounded by the charming towns of Hunter, Windham, and Tannersville, with chic inns, boutique hotels, and endless adventures nearby, Hayfield offers couples and their guests a full Catskills experience: refined, romantic, and impossibly memorable.
Photography by: O’Malley Photographers and others
Matilda
Matilda is a culinary love letter to the Catskills – an elegant yet grounded restaurant where fine dining meets the region’s natural abundance. Led by acclaimed New York chefs Jeremiah Stone and Fabián von Hauske Valtierra of Wildair and Bar Contra, Matilda captures the raw beauty of its mountain surroundings through food that’s both comforting and quietly daring. Set within The Henson, a lovingly restored 16-room inn, the restaurant extends the hotel’s philosophy of thoughtful hospitality—where every detail, from design to dining, reflects a deep appreciation for place. Golden light filters through garden windows, soft fabric lamps glow beside a limewashed fireplace, and guests linger in a space that feels both contemporary and timeless.
The menu celebrates the Catskills’ rhythm and seasonality, drawing ingredients from a close-knit network of local farmers, foragers, and producers. Dishes like steelhead trout with nori purée and sea beans, slow-grilled chicken with tomato béarnaise, and the playful potato and strawberry mousse reflect both the chefs’ city-honed precision and their reverence for the land. Each plate is designed to surprise and delight in equal measure – “comforting and challenging,” as co-owner Ely Franko describes it. The beverage program mirrors this sensibility, with a 40-bottle wine list spanning the old and new worlds, alongside refined cocktails such as the Iron Goddess and Grannies on Acid crafted in collaboration with Dave Arnold.
Ultimately, Matilda is more than a restaurant, it’s a celebration of connection. Between the people who grow the food and those who prepare it, between travelers and locals who gather at its tables, and between the timelessness of the mountains and the creativity of those who call them home. Whether you come for a date night, a lingering dinner with friends, or cocktails on the sunlit porch overlooking the garden, Matilda invites you to savor the moment and rediscover what dining in the Catskills can be.
The Henson
Nestled in the heart of the Catskills, The Henson is a lovingly restored 19th-century inn that embodies the spirit of this storied landscape—unassuming, beautiful, and deeply human. Once a humble boarding house, the inn has been reborn as a refined yet approachable retreat, blending history with a sense of modern serenity. Each of its sixteen rooms is designed for comfort and calm, with warm light, natural textures, and thoughtful touches—from Casper mattresses and Frette towels to rainfall showers and Grown Alchemist amenities. Whether it’s a morning spent watching the mist rise over the mountains, an afternoon curled up by the fire, or a long evening under the stars, every moment at The Henson invites guests to slow down and feel at home.
Winner, Condé Nast Traveler Hot List - The Best New Hotel Openings In The World and Esquire Magazine - The Best New Hotels In The World
Beyond its doors, The Henson offers a world of discovery and delight. The gardens are a living expression of the Catskills’ abundance, with native wildflowers, herbs, and edibles that evolve through the seasons. The living room and library welcome quiet reflection and convivial conversation alike, while the rooftop and wellness room offer views, stillness, and renewal. Events here take on a sense of timeless intimacy—whether a wedding framed by mountain vistas, a family celebration in the private dining room, or a weekend spent reconnecting with friends in a space that feels entirely your own.
“I felt I saw something new and beautiful everywhere I turned at the Henson...It's a beautiful landing pad for everything the Catskills has to offer.” – Architectural Digest
At the heart of The Henson’s culinary experience is Matilda, the on-site restaurant led by acclaimed chefs Jeremiah Stone and Fabián von Hauske Valtierra of New York’s Bar Contra and Wildair. Their menu celebrates the region’s bounty with sincerity and imagination, pairing vibrant local ingredients with a sense of place and purpose. It’s an invitation to gather, to share, and to marvel at the beauty of good food and good company. More than a stay, The Henson is a state of mind—rooted in the landscape, shaped by its history, and alive with the warmth of those who come seeking something real.
Windham Mountain Club
Windham Mountain Club in Windham, NY, is a premier four-season destination offering world-class skiing and year-round outdoor adventures. With 54 trails across 285 skiable acres and high-speed lifts, the resort provides an exceptional winter sports experience for all skill levels. Beyond skiing and snowboarding, guests can enjoy snowshoeing, tubing, and apre-ski relaxation in the resort's upscale dining and lounge areas.
Accommodations at Windham Mountain Club feature luxury ski-in, ski-out condos with stunning mountain views, private gyms, heated pools, and hot tubs. Dining options range from the Italian-inspired Cin Cin! to the slopeside Sushi Bar Okami and the elevated Foodhall, offering locally sourced cuisine. In the warmer months, the resort transforms into a hub for mountain biking, hiking, and golf at Windham Country Club, making it a perfect year-round retreat in the heart of the Catskills.
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