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Things To Do In Dutchess County During A Weekend Escape From NYC


Modified: December 27, 2023

by Eudora Aaron



Welcome to Dutchess County, a beautiful getaway destination located just a stone’s throw away from the bustling streets of New York City. Nestled in the heart of the Hudson Valley, Dutchess County offers a perfect blend of natural beauty, rich history, and delicious culinary experiences. Whether you’re looking for a weekend trip or a longer escape, this charming region has something for everyone.


Just a short drive or train ride from NYC, Dutchess County feels like a world away from the city’s hustle and bustle. With its picturesque landscapes, quaint towns, and friendly locals, it’s the ideal destination for those seeking a peaceful retreat and a chance to reconnect with nature.


So, grab your bags, hit the road, and get ready to embark on an unforgettable weekend adventure in Dutchess County. From exploring historic sites to enjoying outdoor activities and indulging in mouth-watering food and wine, this article will guide you through the best things to do during your escape. Let’s dive in and discover the hidden gems of this charming region!


Day 1: Exploring Historic Sites

Start your weekend escape by immersing yourself in the rich history of Dutchess County. This region is home to a plethora of historic sites that offer a glimpse into the past. Begin your day by visiting the Franklin D. Roosevelt Presidential Library and Museum in Hyde Park. Explore the exhibits that showcase the life and legacy of the 32nd President of the United States and gain insight into his impactful presidency.


Next, head over to the Vanderbilt Mansion National Historic Site, also located in Hyde Park. Take a guided tour of this opulent Gilded Age mansion, once home to the prominent Vanderbilt family. Marvel at the stunning architecture, luxurious interiors, and beautiful gardens as you learn about the lavish lifestyle of the elite class in the early 20th century.


Continue your historical journey by visiting the Home of Franklin D. Roosevelt National Historic Site. Explore the Springwood estate, FDR’s ancestral home, and gain a deeper understanding of his personal life and connection to the Hudson Valley. Don’t miss the chance to stroll through the rose garden and enjoy the tranquil ambiance.


For a taste of Dutchess County’s colonial past, make a stop at the Old Rhinebeck Aerodrome, located in Rhinebeck. Step back in time as you witness vintage planes take to the skies in thrilling aerial shows. Explore the museum’s collection of early aviation artifacts and watch reenactments of historic air battles. It’s a truly immersive experience that will transport you to the early days of aviation.


As the day comes to a close, immerse yourself in the scenic beauty of Dutchess County by visiting the Walkway Over the Hudson. This pedestrian bridge, spanning the Hudson River, offers breathtaking views of the surrounding mountains and the river below. Take a leisurely stroll or rent a bike to fully appreciate the splendor of the Hudson Valley’s landscape.


After a day filled with exploration and historical marvels, unwind and relax at one of Dutchess County’s charming bed and breakfasts or boutique hotels. Rest up, for there’s more adventure awaiting you on Day 2.


Day 2: Enjoying Outdoor Activities

Wake up refreshed and ready to embrace the great outdoors in Dutchess County. With its abundance of parks, trails, and natural beauty, this region offers a wide array of outdoor activities for nature enthusiasts.


Start your day by exploring the stunning grounds of the Innisfree Garden in Millbrook. This well-preserved Chinese-inspired garden is a sanctuary of tranquility, featuring a series of ponds, streams, and meticulously manicured landscapes. Take a leisurely stroll along the winding paths, breathe in the fresh air, and admire the harmonious beauty of this hidden gem.


Continue your outdoor adventure by visiting the Minnewaska State Park Preserve in Kerhonkson. Hike along the scenic trails that wind through breathtaking landscapes, including rugged cliffs, pristine lakes, and cascading waterfalls. Explore the picturesque Awosting Falls or challenge yourself on the challenging Gertrude’s Nose Trail for panoramic views of the surrounding valleys.


If you’re a fan of adrenaline-pumping activities, make sure to try rock climbing at the Shawangunk Mountains, also known as the Gunks. This world-renowned climbing destination offers a variety of routes for climbers of all skill levels. Feel the thrill as you conquer the cliffs and take in the breathtaking vistas from the top.


For a more leisurely outdoor experience, head to the Dutchess Rail Trail. This scenic trail spans over 13 miles and is perfect for walking, jogging, or cycling. Meander through picturesque landscapes, historic landmarks, and charming towns as you connect with nature and enjoy the region’s beauty at a relaxed pace.


In the afternoon, treat yourself to a relaxing boating experience on the Hudson River. Rent a kayak or a paddleboard and explore the waterways at your own pace. Drink in the sweeping views of the lush riverbanks, spot wildlife, and relish the serenity of the surroundings.


As the sun sets, indulge in a romantic dinner at one of Dutchess County’s farm-to-table restaurants. Sample the region’s fresh and locally sourced ingredients while savoring delicious dishes prepared by talented chefs. Pair your meal with a glass of wine from one of the local wineries for the perfect ending to your outdoor adventure.


After a fulfilling day of exploring nature’s wonders, relax and recharge for the final day of your weekend escape in Dutchess County.


Day 3: Indulging in Food and Wine

On your final day in Dutchess County, immerse yourself in the region’s vibrant culinary scene. Known for its farm-to-table ethos, this area boasts a plethora of local farms, vineyards, and restaurants that offer a delectable array of flavors.


Start your day with a visit to one of the local farmers’ markets. Explore stalls filled with fresh produce, artisanal cheeses, locally baked bread, and much more. Engage with the farmers, learn about their sustainable practices, and pick up some ingredients for a picnic later on.


Next, embark on a wine tasting adventure at one of the many wineries scattered throughout the Hudson Valley. Discover the rich flavors of locally produced wines as you explore the vineyards and take in the stunning views of the rolling hills. From crisp whites to robust reds, there’s a wine for every palate.


After indulging in some wine, satiate your appetite at one of the region’s renowned farm-to-table restaurants. Many of these establishments pride themselves on sourcing ingredients from local farmers and incorporating them into their seasonal menus. Let your taste buds dance with each bite of fresh, flavorful dishes that showcase the best of Dutchess County’s culinary offerings.


For a unique food experience, consider taking a culinary class or joining a farm tour. Learn about sustainable farming practices, try your hand at making artisanal products such as cheese or honey, and gain a deeper appreciation for the farm-to-table movement. It’s a hands-on experience that connects you with the local food culture.


In the afternoon, enjoy a leisurely drive through the picturesque countryside, stopping at charming roadside stands and quaint shops along the way. Sample homemade jams, pick up freshly picked berries, or browse through unique handmade crafts as you soak in the delightful atmosphere of Dutchess County’s small towns.


As the day winds down, find a scenic spot for a picnic and enjoy the fresh local ingredients you purchased earlier. Bask in the beauty of the Hudson Valley’s landscapes as you savor the flavors of the region. Reflect on the memories you’ve created during your weekend escape in Dutchess County.


Before bidding farewell to this enchanting region, don’t forget to pick up some locally sourced goodies to take home as souvenirs. Whether it’s a bottle of wine, a jar of artisanal honey, or a bag of freshly roasted coffee, these unique products will serve as a reminder of your culinary journey in Dutchess County.


As you head back to New York City, be sure to take a fond and nostalgic look at the memories you’ve made and the adventures you’ve experienced during your weekend escape. Dutchess County will always be ready to welcome you back for another memorable visit!



Dutchess County provides the perfect weekend escape from the bustling streets of New York City. This charming region, with its rich history, stunning landscapes, and delectable culinary delights, offers a diverse range of experiences for every visitor.


From exploring historic sites that shed light on the nation’s past, to immersing oneself in the natural beauty of parks, trails, and gardens, Dutchess County has something to captivate every traveler. The region’s commitment to sustainable farming practices and farm-to-table dining ensures that food enthusiasts will be delighted with the fresh and flavorful local cuisine.


Whether you’re a history buff, an outdoor adventurer, a foodie, or simply seeking a peaceful getaway, Dutchess County’s diverse offerings will meet your desires. The region’s proximity to New York City makes it an easily accessible destination for a weekend escape.


So, pack your bags, hit the road, and embark on an unforgettable journey through Dutchess County. Explore historic sites, embrace the great outdoors, indulge in delicious food and wine, and create lasting memories in this idyllic corner of the Hudson Valley. Discover the beauty, charm, and warmth of Dutchess County and return to the city feeling refreshed and rejuvenated.


But beware, Dutchess County has a way of capturing your heart and leaving you yearning for more. So, until your next visit, cherish the memories and hold on to the spirit of this extraordinary destination. Dutchess County will be waiting to welcome you back with open arms.