Sleepy Hollow

Day Trips

Arrive in Sleepy Hollow, check into your cozy accommodation, and enjoy a leisurely breakfast at a local café. Savor a warm cup of coffee and freshly baked pastries while soaking in the quaint atmosphere. Stroll around the picturesque village to get your bearings and appreciate the charming architecture.

Visit the famous Sleepy Hollow Cemetery, where Washington Irving, author of 'The Legend of Sleepy Hollow,' is buried. Explore the beautiful grounds and captivating gravestones, learning about the legends associated with the area. Next, head to the nearby Philipsburg Manor, a historic site that offers a glimpse into colonial life with its guided tours and reenactments.

End your day with a sunset walk along the Hudson River waterfront. Enjoy the breathtaking views as the sky transforms into vibrant colors. Finish with dinner at a local restaurant offering farm-to-table dishes while recounting your day's adventures.

Start your day with a guided tour of the Old Dutch Church, a historic landmark steeped in local lore. Discover stories of the past as you admire the stunning architecture and tranquil surroundings. Next, make your way to the nearby Sleepy Hollow State Park for a scenic morning hike.

After lunch, visit the Sleepy Hollow Lighthouse, also known as Tarrytown Lighthouse, to soak in majestic views of the Hudson River. The short hike to the lighthouse is invigorating, and you'll have the chance to capture stunning photographs. Return to town for a visit to the Sleepy Hollow Historical Society to learn more about the rich history of the area.

Enjoy a themed dinner at a restaurant inspired by Washington Irving's tales, complete with hearty meals and unique cocktails. Immerse yourself in the atmosphere while enjoying live music or storytelling that echoes the haunting legends of Sleepy Hollow. Wind down your evening with a candlelit ghost tour of the town, led by a local guide who will share eerie tales.

Start your day at the Rockefeller State Park Preserve, where you can explore the tranquil landscapes and picturesque trails. Enjoy birdwatching and perhaps spot some local wildlife as you walk along the serene paths. Have a picnic breakfast in this nature-filled haven, surrounded by scenic views.

In the afternoon, head back into town for a visit to the nearby Kykuit, the Rockefeller estate, known for its stunning gardens and art collections. Join a guided tour to learn about the history of the estate and see the beautiful art pieces collected over the years. Take your time exploring the estate's expansive grounds, soaking in the artistry and tranquility.

Dine at a farm-to-table restaurant that captures the essence of the Hudson Valley's culinary scene. Experience seasonal dishes paired with local wines as you reflect on your day's adventures. Spend your evening relaxing by the river, enjoying the starry night sky and the gentle sounds of the water.

Explore the local artist community with a visit to the Blue Hill Troupe's rehearsal or an art exhibit in one of the local galleries. Engage with artists and learn about their inspirations while appreciating vibrant works. Grab brunch at a nearby café that showcases local art as décor.

Visit the Philipsburg Manor once again, this time participating in one of their hands-on workshops. Learn crafts or historical cooking methods while reveling in the immersive experience. The afternoon could also include a scenic boat ride on the Hudson River for a different perspective of the iconic skyline.

Attend a live performance at the Tarrytown Music Hall, where you can enjoy everything from music to theater. The historic venue adds charm to any show, making for an entertaining night. Conclude your evening with drinks at a cozy lounge nearby, sharing highlights from the show and your trip.

Begin your day with a heart-pumping outdoor adventure such as kayaking on the Hudson River. Marvel at the beautiful scenery and get a unique view of the landscape from the water. After your adventure, enjoy a leisurely brunch at a riverside café.

Spend the afternoon unwinding at the Sleepy Hollow Spa, treating yourself to a massage or wellness treatment. Enjoy the relaxing atmosphere as you take a break from your busy sightseeing schedule. After your spa day, indulge in a light lunch at the spa’s café, savoring healthy dishes.

Conclude your day with a sunset yoga session or a meditation class, which can often be found near the waterfront. The peaceful environment will help you connect with the serene beauty of Sleepy Hollow. Later, share dinner with fellow retreats or make it a romantic evening, feasting on local cuisine by candlelight.

Visit the historic Lyndhurst estate, a grand Gothic Revival mansion surrounded by lush gardens. Take a guided tour of the mansion and learn about its storied past while admiring the stunning architecture. After the tour, take some time to enjoy a leisurely breakfast at the estate's café.

Head to a local farmers' market to discover the best of Hudson Valley produce and artisan goods. Sample fresh fruits, cheeses, and baked goods as you browse the many stalls. Afterward, take a cooking class focused on local ingredients, learning to create dishes inspired by the area.

Celebrate your culinary achievements by enjoying the meal you prepared during the cooking class. Share your creations with fellow participants, making new friends and memories. Wind down your evening with a stroll along the Hudson, reflecting on the delicious experiences of the day.

Start your day with a guided nature walk at the Rockefeller Preserve, focusing on the area's flora and fauna. Breathe in the fresh air while learning about the ecosystem. Enjoy breakfast outdoors, surrounded by the sights and sounds of nature.

Spend your afternoon visiting a local winery for a tour and tasting session, discovering the nuances of Hudson Valley wines. Enjoy a scenic drive through the vineyards, soaking in the picturesque landscapes. Pair your wine tasting with a light lunch at the winery's gourmet bistro.

Return to Sleepy Hollow for a delightful dinner at an upscale restaurant that specializes in wine pairings. Explore new flavor combinations as you savor each course, complemented by expert wine selections. Cap off the night with a leisurely walk while discussing your favorite wines and memorable moments.

Spend your final morning revisiting your favorite spots or exploring any hidden gems you may have missed. Enjoy one last breakfast at a local café, taking in the cozy ambiance and friendly faces. Take a moment to reflect on your adventures in Sleepy Hollow as you soak in the surrounding beauty.

Before departing, make one last stop at the Sleepy Hollow Farmer's Market, where you can purchase local goods and souvenirs. Stock up on delicious snacks, artisanal products, and handmade crafts to take back home. Enjoy a leisurely stroll along the riverbank, soaking in the last sights and sounds of the Hudson.

As you prepare to leave Sleepy Hollow, reflect upon the memories made during your stay. The captivating history and stunning landscapes are sure to stay with you long after you've returned home. Depart with a sense of fulfillment, already dreaming of your next visit to this enchanting town.