Shrub Oak, New York

Three-Day Weekend Trip to Shrub Oak, New York

Welcome to Shrub Oak, a charming town located in Westchester County, New York! Known for its beautiful scenery, historical landmarks, and delicious dining options, Shrub Oak is the perfect destination for a relaxing three-day weekend trip with friends. Get ready to explore the hidden gems of this small but vibrant town.

Day 1: Historical Delights and Natural Beauty

Start your first day in Shrub Oak by immersing yourself in the town’s rich history and enjoying its picturesque surroundings.

Morning: Travel Back in Time at the John Jay Homestead

Begin your day with a visit to the John Jay Homestead, the historic home of John Jay, one of America’s Founding Fathers. Take a guided tour of the house and learn about Jay’s significant role in shaping the nation’s early history. Stroll through the beautifully manicured gardens and enjoy the serene ambiance of this enchanting property.

Lunch: The Black Cow

For a delightful lunch experience, head over to The Black Cow. This charming eatery offers a diverse menu with options for everyone. From homemade soups and gourmet sandwiches to fresh salads and mouthwatering burgers, The Black Cow is a local favorite. Be sure to try their delicious milkshakes, made the old-fashioned way!

Afternoon: Explore Blue Mountain Reservation

After lunch, venture into the great outdoors and discover the natural beauty of Blue Mountain Reservation. This expansive park offers a variety of trails suitable for all skill levels, making it perfect for hiking, biking, or simply enjoying a leisurely walk amidst nature. Keep your eyes peeled for wildlife and take in the breathtaking views of the surrounding mountains.

Dinner: Peter Pratt’s Inn

For a memorable dining experience, make your way to Peter Pratt’s Inn. Housed in a restored 1780s farmhouse, this cozy restaurant serves up delectable farm-to-table cuisine. Indulge in seasonal dishes made with locally sourced ingredients, paired with a fine selection of wines. The rustic charm and warm hospitality of Peter Pratt’s Inn will leave a lasting impression.

Day 2: Artistic Exploration and Culinary Delights

On your second day in Shrub Oak, immerse yourself in the local art scene and indulge in the town’s culinary offerings.

Morning: Peekskill Art District

Start your day with a visit to the Peekskill Art District, just a short drive from Shrub Oak. This vibrant neighborhood is home to numerous art galleries and studios, showcasing the works of talented local artists. Spend some time exploring the diverse exhibits and perhaps even meet some of the artists themselves. Don’t forget to support the local art community by purchasing unique pieces as souvenirs.

Lunch: Gleason’s Restaurant

For a hearty lunch, make your way to Gleason’s Restaurant, a beloved establishment in Peekskill. Known for its comforting American fare, this family-owned eatery offers an extensive menu featuring everything from juicy steaks and fresh seafood to flavorful vegetarian options. The friendly atmosphere and homey vibe make Gleason’s a perfect spot to relax and refuel.

Afternoon: Hudson Valley Center for Contemporary Art

Continue your artistic exploration at the Hudson Valley Center for Contemporary Art. This contemporary art museum showcases thought-provoking exhibitions featuring both established and emerging artists. Take your time to appreciate the diverse range of artworks and engage in meaningful conversations about contemporary culture and society.

Dinner: The Quiet Man Public House

Cap off your day with a visit to The Quiet Man Public House, a charming Irish pub located in Peekskill. Enjoy a cozy atmosphere, live music, and an extensive selection of craft beers and spirits. Delight your taste buds with traditional Irish dishes such as fish and chips, shepherd’s pie, or bangers and mash. The lively ambiance and warm hospitality at The Quiet Man will make for a memorable evening.

Day 3: Outdoor Adventures and Local Flavors

On your final day in Shrub Oak, embrace the great outdoors and savor the local flavors that this region has to offer.

Morning: Fahnestock State Park

Kick-start your day with a visit to Fahnestock State Park, a haven for outdoor enthusiasts. This expansive park offers a range of recreational activities, including hiking, fishing, boating, and camping. Explore the well-marked trails, breathe in the fresh air, and revel in the natural beauty surrounding you.

Lunch: Valley Restaurant at The Garrison

For a gourmet lunch experience, head to The Garrison, a stunning resort nestled in the Hudson Highlands. Indulge in a delightful meal at the Valley Restaurant, which boasts panoramic views of the Hudson River Valley. The menu features seasonal, locally sourced ingredients transformed into exquisite dishes that are sure to tantalize your taste buds.

Afternoon: Stonecrop Gardens

Conclude your trip with a visit to Stonecrop Gardens, a hidden gem that spans over 12 acres. This enchanting garden showcases a diverse collection of plants, including alpine flowers, woodland species, and fascinating succulents. Stroll through various themed gardens, explore tranquil ponds, and take in the serene beauty of this horticultural masterpiece.

Dinner: Birdsall House

Finish your three-day adventure in Shrub Oak with a memorable dinner at Birdsall House, a gastropub located in nearby Peekskill. This cozy establishment offers a rotating selection of craft beers, along with a menu featuring inventive dishes prepared with locally sourced ingredients. From juicy burgers and mouthwatering flatbreads to delectable vegetarian options, Birdsall House has something for everyone.

As your three-day weekend trip comes to a close, you’ll leave Shrub Oak with a sense of tranquility, inspiration from the local art scene, and a taste of the region’s culinary delights. Shrub Oak may be small, but it’s brimming with hidden treasures that are just waiting to be discovered.

Please note that some attractions and restaurants may have specific COVID-19 guidelines and restrictions in place. It is advisable to check their websites or contact them directly for the most up-to-date information.

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