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Guide to the Perfect Autumnal Road Trip

Date Published: September 28, 2020

These days, many of us are craving a change of scenery - whether that means getting out of town or creating a special staycation! We’re breaking down the perfect fall road trip through every region of Dutchess – Northern, Central, Southern or Eastern. Enjoy changing leaves, farm life, food and more. With options that will satisfy a daytrip or overnight stay, we’re happy to welcome you. 

No car? No problem! Some of our local train stations provide access to ZipCar, so you can take the rail to the road!

Want to stay the night? Visit our Where To Stay page and filter by town to browse a variety of lodging options.


Things To Do

Wake up in Dutchess, grab a cup o’ joe, breathe in the fresh air and enjoy the scenic beauty. What better way to start your day than by moving your body and clearing your mind. Whether you set out to take in the views from the Ferncliff Forest Fire Tower in Rhinebeck, hit the water on a kayak in Tivoli Bays, or saunter around Poets' Walk Park in Red Hook – getting outside is the best way to take in the seasons foliage. 

What says fall more than apple or pumpkin picking?! Northern Dutchess has nearly two dozen you-pick farms, plus stands and stores to stock up on local goods. Venture out into the orchards at Greig Farm in Red Hook as you take in views of the Catskill Mountains. Both apple and pumpkin picking are available. Check their website to find out the picking schedule. Keep busy by watching the adorable pygmy goats, strolling the farm trails, or grabbing a bite at the cafe, and exploring the craft market. Mead Orchard in Tivoli offers 40 varieties of apples, winter squash, pumpkins and gourds, with their farm stand open on weekends for those who’d prefer pre-picked produce. See our full guide to pick-your-own farms here.

Photo of Greig Farm

Keep it cultured by heading to The CENTER for Performing Arts at Rhinebeck, presenting performances and drive-in experiences. Or discover Dutchess’ rich past; many of our historical sites’ typical indoor tours are currently closed, but you can still enjoy many of their expansive grounds like at the Home of Franklin D. Roosevelt National Historic Site, and Vanderbilt Mansion National Historic Site in Hyde Park, or outdoor tours and events at Wilderstein Historic Site in Rhinebeck, and Staatsburgh State Historic Site in Staatsburg.

Where To Eat

Wrap up your day with a memorable meal at Terrapin Restaurant & Catering in Rhinebeck, a former church turned restaurant serving unbelievably local, organic cuisine featuring fall flavors. Enjoy a farm-to-table, Mediterranean-inspired meal at The Corner, located on the ground floor level of Hotel Tivoli. Or taste award-winning authentic Mexican fare at Santa Fe – also in Tivoli. Are you vegan, vegetarian, or just keeping things plant-based these days? Try Cinnamon Indian Cuisine in Rhinebeck for fresh dishes like mango salad, veggie samosas and coconut rise.

Photo of Cinnamon Indian Cuisine


Things To Do

If you’re visiting Dutchess during the fall months, I’m sure leaf peeping is on your list! What better place to view nature's bursts of color than the Walkway Over the Hudson State Historic Park - the longest, elevated pedestrian bridge in the world, and former railroad bridge built in 1888. The bridge spans 1.28 miles and stretches 212 feet above the majestic Hudson River, providing a magnificent birds' eye views of the beautiful Catskill Mountains. Would you prefer to be on the river, rather than above it? Book a Fall Foliage Boat Tour by Hudson River Cruises with a special departure from Waryas Park in Poughkeepsie.

In Central Dutchess, the spirited Queen City of Poughkeepsie is going through a twenty-first century revival and pulsing with energy. Head to the heart of it at 40 Cannon, the former King’s Court Hotel now beautifully restored featuring Cafe 40 & Co, Gallery 40, King’s Court Brewing Company and 1915 Wine Cellar. If you’re looking to escape the hustle and bustle, consider visiting a farm brewery. That’s right, Plan Bee Farm Brewery pours ground-to-glass brews that are made using only New York State ingredients, many of which are grown right on site!

Photo of Plan Bee Farm Brewery

Where To Eat

Someone once said that the best way to get to know a place is to eat your way through it, and we agree! Cozy up at Essie’s Restaurant in the City of Poughkeepsie, owned by graduate of The Culinary Institute of America and executive chef, Brandon Walker. His modern American menu is inspired by seasonal ingredients, global flavors and his family roots - the Caribbean and American South. Visit Lolita’s, another City of Poughkepsie spot, for tasty wood fired pizzas and homemade pastas, or visit the legendary Rossi’s Deli for mouthwatering Italian sandwiches and paninis. Looking for dishes that pack a punch? Try out Twisted Soul Concepts for elevated street food with bold flavors like steamed dumplings, empanadas, or their popular noodle bowls.


Things To Do

One of the largest exhibition spaces in the U.S., Dia Beacon presents contemporary art from the 1960s to the present, as well as special exhibits, new commissions and educational programs. They’re currently running on a reservation system to comply with social distancing guidelines, so make yours ahead. Stroll up to Main Street to catch live glassblowing and purchase unique pieces at Hudson Beach Glass, located in a renovated, historic firehouse-turned-shop. Take to the river and hop aboard the Estuary Steward to Pollepel Island for a tour of Bannerman’s Castle - a Scottish-style castle built in the early 1900s to store military surplus, offering great views of the river and surrounding waterfront. Tours leave from the Beacon Institute Floating Dock. Head to higher heights by hiking Mount Beacon, a great hike for scenic sights. Enjoy orchard views while sipping on farm fresh cider at Treasury Cider at Fishkill Farms - it doesn't get fresher than this tree-to-bottle experience!

Photo of Bannerman Castle

Where To Eat

Booming with culinary concepts, Southern Dutchess offers dining options for special occasions and casual eats alike. Check out a not-so-secret, local spot, The Beacon Daily for one of their mind-blowing, hand-crafted English Muffin breakfast sandwiches. Have a taste of Belgian-inspired meals at The Dutchess Biercafe in Fishkill. Looking for a romantic Italian setting? Then dine down the street at Sotano Food & Wine.


Things To Do

Defined by the Harlem Valley, Eastern Dutchess offers the nature-lover countless opportunities to breathe in the open air. Choose from trails like the Appalachian Trail, Dover Stone Church, or Harlem Valley Rail Trail. Experience farm life and pick-your-own at Dykeman Farm in Pawling, or shop the season’s local harvest at Locust Hill Market in Millbrook, stock up on maple syrup at Soukup Farms, or don’t miss out on the most delicious cheeses at Brookby Farm, both located in Dover Plains. End your day by catching a flick under the stars in Amenia at Four Brothers Drive-In Theatre.

Photo of Harlem Valley Rail Trail

Where To Eat 

After working up an appetite, grab a booth at local favorite McKinney & Doyle in Pawling, serving up “serious cuisine in a not-so-serious atmosphere.” Vinny’s Deli is also a staple, and featured on “Food Network” for  their famous Steak Margarita sandwich. Pick up a bite at Harney & Sons Tea Shop in Millerton, open Friday's through Sunday's for takeout. Be sure to peep their seasonal teas, like Cranberry Autumn on their online shop! Keep is cozy at Babette’s Kitchen in Millbrook where they are dedicated to featuring local, seasonal ingredients in salads, quiches and specialty sandwiches.

To see our full Dutchess Destination Guide, click here.

For more road trip inspiration, see these blogs below:

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