14 Incredible Things To Do During A Long Weekend In Poughkeepsie, New York (2024)

Located about halfway between New York City and Albany, Poughkeepsie is a picturesque town on the east bank of the Hudson River. It offers outdoor adventure, breathtaking views, rich history, and delicious farm-to-table eateries. Here’s how to spend an incredible long weekend in Poughkeepsie, New York.

Things To Do In Poughkeepsie

1. Stroll Across The Hudson River

If strolling across the Hudson River is on your Upstate New York bucket list, the town of Poughkeepsie offers two options: Walkway Over the Hudson and the Mid-Hudson Bridge.

Formerly the Poughkeepsie-Highland Railroad Bridge, the Walkway Over the Hudson is the world’s longest elevated pedestrian bridge. Its ADA handicapped-accessible multi-use path is open to walkers, joggers, and cyclists year-round from 7:00 a.m. to sunset. Visitors can explore discovery zones on both sides of the Hudson, including Highland Hamlet, Franny Reese State Park, Little Italy, and the Southside Historic District.

Although it is a road shared with multiple lanes of traffic, the pedestrian path on the north side of the Franklin D. Roosevelt Mid-Hudson Bridge connects to the Walkway Loop Trail and offers the same beautiful panoramic views of Poughkeepsie, the Catskill Mountains, and the tree-lined Hudson River. The scenery is most spectacular at sunrise and sunset when fall foliage is at its peak.

Pro Tip: While cyclists can bike across the Walkway Over the Hudson, they need to dismount and walk their bikes over the Mid-Hudson Bridge.

2. Bike The Dutchess Rail Trail

To further explore the Poughkeepsie area on two wheels, hit the William R. Steinhaus Dutchess Rail Trail. This 13.4-mile paved trail runs from the Hopewell Depot to the Walkway Over the Hudson. As Dutchess County blends into Ulster County halfway across the bridge, the path continues to wind along the river as the Hudson Valley Rail Trail.

If you need to rent a bike in Poughkeepsie, City Bike Rentals is conveniently located about a mile east (about a seven-minute bike ride) of the right bank on the ramp to the Walkway Over the Hudson.

Pro Tip: If your time is limited, Poughkeepsie is a fantastic day trip from New York City just two hours north of the Big Apple.

3. Climb Mount Beacon Fire Tower

If you’d rather walk uphill (than across the Hudson River) to enjoy scenic views of the Hudson River, then the Mount Beacon Fire Tower is for you! Begin the trek with a staircase that parallels the Beacon Incline Railway, once the world’s steepest funicular. Then, continue winding your way along switchbacks for a mile until you reach the fire tower. Once you scale the 60-foot structure, you’ll be treated to an impressive view that lets you see both Manhattan and Albany on a clear day.

Pro Tip: Here are more of my favorite quaint towns on the Hudson River.

4. Tour Samuel Morse’s Home

The scenic river valley that attracted Rockefellers and Vanderbilts to build lavish vacation homes also appealed to Samuel Morse. Inspired by his travels in Southern Europe, the inventor of the telegraph and Morse Code built a mansion in Poughkeepsie on a bluff spanning 200 acres overlooking the Hudson River.

While you may know him from history books as the man who revolutionized global communication in the mid-1800s, Morse was originally a painter with a deep admiration for the Italian countryside. From his former home to the flower and vegetable gardens that surround it, you’ll see hints of old Italy throughout. When you visit, tour the historic mansion, wander through the gardens, or hike the old carriage roads that wind through shady groves and open meadows.

Pro Tip: Locust Grove is not ADA accessible. Be prepared to scale several steps to the front door and a flight of stairs to the second floor when visiting.

5. Visit Top Cottage, An Accessible Retreat

It’s easy to understand how a man leading the nation through the depth of the Great Depression and the horrors of World War II might seek an escape from the bright spotlight of the global press and the pressures of office. However, when you’re confined to a wheelchair in the mid-1900s, fewer options are available to you.

Top Cottage is a Dutch colonial designed by President Franklin D. Roosevelt to accommodate his wheelchair. Not only is it a rare building designed by a sitting president (Jefferson’s Monticello is the only other), but when it was built in the late 1930s, it was one of the first buildings in the country designed by and for a person with a disability. Although Roosevelt cherished Top Cottage as a place he could rest and recharge with greater independence, he did invite close friends and political allies from time to time, including King George VI, Queen Elizabeth II, and Winston Churchill.

Pro Tip: In addition to this wooded retreat in Poughkeepsie where the Roosevelts welcomed heads of state and other distinguished guests, you can visit two other Roosevelt homes in nearby Hyde Park. Springwood is President Roosevelt’s childhood home that was known as the “Summer White House” during the 12 years FDR was in office. Val-Kill Cottage is a factory turned home frequented by Eleanor Roosevelt.

6. Support A Hudson Valley Farmer

One of the benefits of visiting a fertile agricultural area like the Hudson River Valley is the chance to enjoy farm-fresh produce, pasture-raised meats, artisan cheeses, and freshly-baked bread. Shop a wide variety of locally produced agricultural products at Taste of NY at Todd Hill. The year-round market offers milk, eggs, cheese, honey, fresh meat, and many other items that change seasonally. The farm stand at Barton Orchards sells apple cider donuts, apple dumplings, and apple strudel along with many other offerings. Pick up fresh produce at the Adams Fairacre Farms store. Although this family-owned supermarket now has four locations in the Hudson Valley, the Poughkeepsie store is built on the original Adams farm.

7. Enjoy A Picnic With Waterfront Views

Pack a picnic with a charcuterie board of meat and cheese, fresh bread, seasonal fruit, and a homemade pie, then head outdoors to enjoy your farm-to-blanket meal al fresco. Poughkeepsie offers several picturesque spots with waterfront views, including Walkway Over the Hudson State Historic Park, Upper Landing Park, and Peach Hill Park.

Pro Tip: To explore several Hudson Valley towns without changing hotels every night, Poughkeepsie is a great central location. Not only is it halfway between Tarrytown and Hudson on the river’s east bank, but the Mid-Hudson Bridge also provides easy access to the town on the left bank of the Hudson River.

Best Restaurants In Poughkeepsie

8. The Poughkeepsie Grind

Start your day with a local favorite where the coffee beans are roasted on-site and the food is made to order. If you love waffles, the Poughkeepsie Grind is the place for Belgian-style waffles made from scratch daily. Try one covered with fresh fruit, chocolate, or topped with bacon and eggs.

9. Shadows On The Hudson

Perched on a cliff above the Hudson River, this waterfront restaurant is one of the best spots in Poughkeepsie for brunch. The buffet at Shadows on the Hudson includes both breakfast and lunch items, including a made-to-order omelet bar, a carving station with strip loin, turkey breast, honey-glazed ham, and an extravagant dessert display.

10. Farmers And Chefs

Pairing farm-fresh ingredients with talented culinary artists, Farmers & Chefs is a great spot for lunch or dinner in Poughkeepsie. Share a cheese and charcuterie platter, bite into a grass-fed beef burger, or enjoy pan-roasted duck breast. They also offer delicious craft co*cktails like Bohemian passion with white rum, triple sec, coconut cream, and pink grapefruit juice.

11. Bluestone Kitchen And Bar

With its debut in early 2022, Bluestone Kitchen + Bar is relatively new to the Poughkeepsie food scene. Owned and operated by three Hudson Valley locals, it offers a wide range of brunch, lunch, and dinner items for folks visiting Poughkeepsie with special diets or traveling with a food allergy.

12. Mill House Brewing Company

For local beers on tap and a wide-ranging all-day menu, Mill House Brewing Company is the place to go in Poughkeepsie. Enjoy classic brew pub appetizers like fried pickle chips and pretzel bites, filling dinner salads, a variety of burgers, sandwiches, and more.

Best Hotels In Poughkeepsie

13. Hyatt Place Poughkeepsie

Conveniently located about ten minutes from both Vassar College and downtown, Hyatt Place Poughkeepsie is a relatively new, clean, and comfortable place to stay. It is pet friendly, and the back of the property faces thick woods that are especially beautiful as the leaves change colors in the fall. Request a room on a high floor for the best views.

14. Homewood Suites By Hilton Poughkeepsie

Just south of Locust Grove, each room at the Homewood Suites by Hilton includes a fully equipped kitchen with separate living and sleeping areas. The hotel grounds include a basketball court, putting green, and a beautiful outdoor seating area with a fire pit.

Whether your visit to Poughkeepsie is a weekend getaway or part of a longer Hudson Valley road trip, you’ll find plenty of incredible things to see and do. You’ll also find delicious places to eat when you spend time in this Hudson River town halfway between New York City and Albany.