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See the Hudson Valley by Bike : Poughkeepsie to New Paltz Bike Tour

Poughkeepsie to New Paltz Bike Tour As the Hudson Valley approaches peak foliage, it’s time to hop on a bike and weave your way through little towns and over the Hudson RIver, smelling the crisp fall air and hearing the crunch of leaves under your tires. The Hudson Valley Rail Trail, Walkway Over the Hudson, and the William R. Steinhaus Dutchess Rail Trail link the village of New Paltz on the east to the town of Hopewell Junction on the west. Grab a bike and glide your way through unique Hudson Valley villages, stopping for lunch, drinks, or just to enjoy the views. These three paths provide over 20 miles of trail to explore- and they are wheelchair accessible!

If you don’t have your own bike or blades, stop by Leisure Bike Ride in Poughkeepsie, open 9:30am-7:00pm Monday to Saturday, and 9:30am-6:00pm on Sundays. This bicycle shop rents hybrid bikes, tandem bikes, adult tricycles, surrey family bikes (room for 3 adults and 2 kids, all snug under a canopy), and mountain bikes. Rental prices range from $9 an hour to $15 an hour, depending on the kind of bike you choose. This bike shop makes exploring easy, as it’s just steps away from the Dutchess Rail Trail, and you’re able to leave your car in their parking lot.

Rossis Deli

If food is on your mind, cruise 6 miles north to Rossi’s Rosticceria & Deli in Poughkeepsie. This deli offers the most satiating lunch on a budget. Opt to build your own sand which with fresh baked bread- Rossi’s piles layers of meat and cheese. A small sub on focaccia bread will easily feed two people. Get your sandwich to go and enjoy it on the Poughkeepsie waterfront, in Kaal Rock Park. Look above and you’ll see the Walkway Over the Hudson, your next destination.

Millhouse Brewing

Or, if you’d rather dine in for lunch ride over to Millhouse Brewing, an easy mile away from the walkway and open at 11:30am on weekends. This brew pub brewery hit the ground running in 2013 and has been serving delicious dishes made from local ingredients- with a selection of innovative beers- ever since. Millhouse Brewing has everything from kimchi and shrimp fried rice to brisket with brussel sprouts. One section of their menu is dedicated solely to sausages, and another to a variety of flatbreads. Explore their menu here and get your tastebuds ready for lunch. If you’re in the mood for a beer before you get back on your bike, try their award winning cucumber blessings- a crisp, dry, refreshing brew that seriously tastes like a cucumber and will bring a smile to your face.

Once you’ve finished lunch, head to the Walkway Over the Hudson, the longest elevated pedestrian bridge in the world. If your car transported your bike, park on the east side of the river at 61 Parker Avenue in Poughkeepsie (conveniently located 0.7 miles from the metro north train station), or on the western side at 87 Haviland Rd in Highland. This 1.6 mile pedestrian bridge used to serve as a railway to transport western raw materials to eastern industrial markets back in the late 1800s. In 2016 it was inducted into the Rail Trail Hall of Fame- once you’re on it you can see why. At 212 feet above the Hudson River, you can take in a 360 degree view complete with the Catskill Mountains and long stretches of the river. Breathe deep, feel gratitude for where you are and keep pedaling.

When you reach the other side, you can stray from the rail trail and head down to Franny Reese State Park, where you can take in more Hudson River waterfront views. Or, keep biking and head west, through Highland, Lloyd, and eventually arriving in New Paltz 7 miles later. The trail will drop you at the cross of South St and Route 299. Follow Route 299 3 miles west and you’ll arrive in the quaint little village of New Paltz. Biking on the road will be well worth it, as New Paltz’s streets are lined with vintage and modern boutiques, restaurants, cafes, and plenty of patios to enjoy the warm fall air.

If you skipped lunch in Poughkeepsie, or are ready for another round of drinks, then head to Huckleberry on Church St. It’s clear why this bar and restaurant is a local favorite- there’s cozy seating inside, as well as benches and adirondack chairs circled around a few fire pits outside. Huckleberry serves pub food with a fresh twist. If you’re in the mood for appetizers, order the blistered shishito peppers served with a creamy dipping sauce. For a heartier fare, you can’t go wrong with the grass-fed beef burger or savory Stout Mac n Cheese. Relax and rest your legs by the fire before you resume your ride.


After exploring and shopping at funky, local shops like the Groovy Blueberry and Heady Teddy’s, stop by the Scenic Overlook at the cross of Main St and Huguenot St, right on the Walkill River. This newly constructed space offers an expansive view of the foothills leading up to the Shawangunk Ridge. This view is especially spectacular in the fall when the trees are ablaze with color.

Main Course

Before pedaling back to Poughkeepsie, stop by Main Course for dessert. The seasonal menu at this rustic, cafe style restaurant is simple but so delicious. Sourcing as many local ingredients as possible, Main Course offers healthy, satiating meals at an affordable price. Lucky for you, their dessert menu offers everything from gluten free chocolate cake and chia seed pudding to cheesecakes and a variety of cookies the size of a your hand. Stock up on sweets here for your journey back across the great Hudson River. Remember to wear a helmet and bring plenty of water!


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