Historic Hudson Valley Itinerary: A 2-Night Cultural & Culinary Escape
- Alana
- Jul 14
- 3 min read
Updated: Jul 21
Escape to the Hudson Valley for a weekend steeped in history, culture, and culinary delights. Whether you're searching for the best things to do in the Hudson Valley or planning your perfect Hudson Valley travel guide, this itinerary offers a rich blend of heritage and unforgettable experiences. Nestled in the heart of New Paltz, Watergrasshill B&B provides the perfect home base for exploring the region’s rich past, from Revolutionary-era streets to presidential legacies. This thoughtfully curated historic Hudson Valley itinerary offers a perfect balance of immersive historical experiences and indulgent dining, ensuring a memorable getaway.
Day 1: Arrival & Exploring Historic New Paltz
Visit Mohonk Mountain House- Before checking in, stop at the iconic Mohonk Mountain House to tour their breathtaking grounds and gardens. Wander through lush landscapes, admire scenic mountain views, and enjoy a peaceful introduction to the beauty of the Hudson Valley.
Check-In at Watergrasshill B&B- Arrive at our charming bed and breakfast, built in 1810, the farmhouse has been transformed into a cozy retreat. Take a moment to unwind and soak in the serene surroundings.
Explore Historic Huguenot Street- Step back in time with a visit to Historic Huguenot Street, one of the oldest continuously inhabited streets in America. Walk among beautifully preserved 17th-century stone houses, visit the reconstructed Esopus Munsee wigwam, and learn about the diverse cultures that shaped early New York.
Dinner at a Local Farm-to-Table Restaurant- Cap off your first evening with a delicious meal at one of the Hudson Valley's acclaimed farm-to-table restaurants, where locally sourced ingredients shine in every dish.
Day 2: A Presidential & Culinary Experience in Hyde Park
Breakfast at Watergrasshill B&B- Start your day with a hearty homemade breakfast- think blueberry scones, a garden frittata and savory sausage.
Visit the Franklin D. Roosevelt Presidential Library & Museum- Journey to Hyde Park (about a 35 minute drive) to explore the Franklin D. Roosevelt Presidential Library & Museum. Walk through history as you learn about FDR’s legacy, from the New Deal to World War II, and tour his family home, Springwood, where he was born and raised.
Lunch at the Culinary Institute of America (CIA)- Savor an unforgettable dining experience at one of the renowned restaurants at the CIA in Hyde Park. Whether you opt for a refined French meal at Bocuse or a farm-to-table feast at American Bounty, the expertise of the CIA’s chefs-in-training ensures an exquisite meal.
Explore the Vanderbilt Mansion National Historic Site-After lunch, take a leisurely tour of the Vanderbilt Mansion, a Gilded Age masterpiece offering stunning views of the Hudson River and insights into the opulent lifestyles of America’s elite.
Evening Stroll in New Paltz & Relaxation-Return to New Paltz and unwind with an evening stroll through the charming village. Browse local shops, stop for a cozy nightcap, or simply relax back at Watergrasshill B&B with a good book on the hammock.
Optional Visit: Eleanor Roosevelt's Val-Kill- For those interested in learning more about one of America’s most influential first ladies, consider a visit to Val-Kill, the only National Historic Site dedicated to a First Lady. This charming retreat was Eleanor Roosevelt’s primary residence in later years and offers an intimate look into her life and humanitarian legacy.
Day 3: Departure with a castle visit
Farewell Breakfast at Watergrasshill B&B- Enjoy another homemade breakfast featuring house-made granola, fresh baked goods, and seasonal specialties before bidding farewell to your weekend retreat.
Bannerman Castle Tour on Pollepel Island
For those with a bit more time and a sense of adventure, consider a tour of Bannerman Castle. Accessible only by boat from Beacon or Newburgh, this abandoned early 20th-century arsenal is perched dramatically on Pollepel Island in the middle of the Hudson River. Guided tours offer a glimpse into its quirky history and spectacular views of the surrounding valley—perfect for history buffs and photographers alike.
Optional Stop: Walkway Over the Hudson- If time allows before heading home, take a scenic walk on the Walkway Over the Hudson, the world’s longest elevated pedestrian bridge, offering breathtaking views of the Hudson River Valley.
Plan Your Historic Hudson Valley Getaway
Whether you’re a history buff, a foodie, or simply looking for a unique weekend escape, this itinerary offers the perfect blend of exploration and relaxation. Plan your Hudson Valley getaway at Watergrasshill B&B and experience one of the best historic stays in New York.