Home Blog Frosty Adventures: A Guide to Winter Activities in Sleepy Hollow

Frosty Adventures: A Guide to Winter Activities in Sleepy Hollow

Old Dutch Church

Sleepy Hollow is a town built for the fall and winter, when crisp air envelops the entire atmosphere. In winter, as a shimmering frost covers the town, enjoy everything from historical tours to scenic riverwalks in this charming corner of Hudson Valley. During your stay at Sleepy Hollow Hotel, enjoy your proximity to these spectacular winter activities, which highlight the best the town has to offer. 

Embrace the chilly winter air, put on your coziest scarves and jackets, and join us on a journey through the frost-kissed landscapes of scenic Hudson Valley.

Scenic Hudson Riverwalk Park

Soak in the serenity of the winter season with a scenic walk along the Hudson River. This 5.2-acre park meanders along the bucolic banks of the river, taking you along various snow-covered landscapes. It’s part of the county’s plan to create a 51-mile long RiverWalk. This leisurely winter walk is a perfect way to rejuvenate your spirit and appreciate the natural beauty that Sleepy Hollow offers, all while enjoying the invigorating chill of the season.

Old Dutch Reformed Church

One of Sleepy Hollow’s historic gems, the Old Dutch Reformed Church is a testament to the town’s rich heritage. Dating back centuries, the church’s iconic cemetery β€” an important part of β€œThe Legend of Sleepy Hollow” β€” is magical in the winter especially. As you explore the church grounds, visit the last resting places of notable figures like Washington Irving, Andrew Carnegie, Brooke Astor and more. 

Tarrytown Main Street

Venture just beyond Sleepy Hollow to explore the charming Main Street of nearby Tarrytown. Lined with historic buildings, boutique shops, and cozy cafes, this bustling thoroughfare exudes a festive charm during the winter months. Adorned with twinkling lights and seasonal decorations, Main Street invites you to shop, dine, and experience the warmth of small-town hospitality against a backdrop of winter enchantment.

Tarrytown is also home to many of the area’s best dining establishments, which we have listed here.

Enjoy a meal at the Blue Hill at Stone Barns

Farm-to-table takes on a completely different meaning at Blue Hill at Stone Barns, which boasts two Michelin stars. This elegant, high-end eatery highlights seasonal fare from 64 local farms, creating unique prix-fixe menus that combine unlikely ingredients into an outstanding experience.

Blue Hill at Stone Barns offers both a formal dining room for dinners and a more casual Cafeteria for lunch and cafΓ©-style snacks. You can reserve a table here

Spend your holiday season at Sleepy Hollow Hotel and enjoy everything the town has to offer, from riverside walks to centuries-old estates. Indulge in these activities that showcase the beauty and history of this beloved village. 

After a day of exploration, return to the warmth of our elegant accommodations, where you can unwind and relive the magic of your frosty adventures. Book your stay with us now!