15+ Best Things To Do In Poughkeepsie, New York — The Purposely Lost (2024)

This post may contain affiliate links! I will receive a commission, at no extra cost to you, if you purchase something recommended here.

If you head all the way up the Metro-North Husdon train line from Grand Central Terminal and get off at the last stop, you’ll have reached the city of Poughkeepsie.

Nicknamed “The Queen City of the Hudson” due to its location on the Hudson River, Dutch settlers first established the town.

It rose to prominence after the American Revolutionary War when it was declared as the state of New York’s second capital.

Today, there are so many different things to do in Poughkeepsie, both in town and around the surrounding cities.

I spent 3 days roaming around town, and it was the perfect upstate New York getaway!

Grab your Travel Planner

Planning your next adventure can become overwhelming.Stay organized with this free, printable travel planner!

Best Things to do in Poughkeepsie

1. Visit the colleges

Poughkeepsie is home to three major colleges – Marist College, Vassar College, and the Culinary Institute of America.

Whether you’re looking at universities for yourself or you’re long out of school, take a drive through the school campuses.

Marist College is a liberal arts college that also has a campus in Florence, Italy.

You can take a campus tour or visit their 3,200 square-foot Art Gallery, which features works from regional contemporary artists.

They also have a beautiful sidewalk right along the Hudson River’s edge.

Vassar College was first founded as a women’s school and part of the Seven Sisters colleges, making them a sister institution to the Ivy League and a rival to many male institutes of higher education.

Visit their campus, or tour the Frances Lehman Loeb Art Center, with features more than 22,000 works from all different eras in history.

From its humble beginnings in New Haven, Connecticut, following World War II, to its rise in prominence and expansion to the Hudson Valley in the 1970s, the Culinary Institute of America is considered one of the world’s best culinary colleges.

Take advantage of all the talent surrounding you and dine at one of the on-campus restaurants operated by current students.

2. Take a tour of Samuel Morse Locust Grove Estate

The man. The code. The revolutionary communication method he created.

Samuel Morse was an American artist and inventor who developed the electric telegraph and, later, Morse Code, along with his friend Alfred Vail in the 1830s.

According to Britannica Encyclopedia:

Morse Code, either of two systems for representing letters of the alphabet, numerals, and punctuation marks by an arrangement of dots, dashes, and spaces. The codes are transmitted as electrical pulses of varied lengths or analogous mechanical or visual signals, such as flashing lights.

THE EDITORS OF Encyclopaedia Britannica. “Morse Code.” Encyclopædia Britannica, Encyclopædia Britannica, Inc., 18 Sept. 2020, www.britannica.com/topic/Morse-Code.

In the 1850s, Morse purchased the estate Locust Grove and build an Italian-style villa on the grounds.

He and his family used it as a summer home before selling the property to the Youngs, a wealthy Poughkeepsie family.

Since the Youngs wanted to live in the house full time, they renovated and winterized the house in the late 1890s but never did any major renovations on the house again.

By the time Annette Young, the initial buyers’ daughter, passed away in the 1970s, the house had stayed like a time capsule.

Even now, almost all of the house is still furnished in exactly the same way as it was in the 1890s for the Young family.

Locust Grove Estate is open to the public and available for tours, and our tour guide was incredibly knowledgeable on the history of the house and the people who lived within it.

3. Walk along the Walkway Over the Hudson State Historic Park

As you might know, one of my favorite free things to do in New York City is walk the High Line.

Well, Poughkeepsie’s Walkway Over the Hudson is very similar to its city counterpart – it also was once a railway that has been converted into a public park!

The Poughkeepsie-Highland Railroad Bridge first opened in 1889; at the time, it was the longest bridge in the world.

It carried cargo and passengers throughout its time in operation until a fire destroyed the train tracks in 1974.

Finally, the bridge reopened as the public, elevated pedestrian bridge today as part of the beautiful Hudson Valley Rail Trail Network in 2009, clocking in at 1.28 miles.

The sweeping views from the Walkway Over the Hudson bridge are sensational in all directions.

It feels like, no matter which direction you look, you’re surrounded by nature and its beauty. It was definitely one of my favorite things to do in Poughkeepsie.

As a note to remember, I did the walk in the winter.

While it only took us about an hour to go end to end and back, the wind was fierce, and we were quite cold throughout.

I’m sure the breeze is excellent in the summer to cool you down, though!

4. Visit Poughkeepsie’s Public Parks

In addition to Walkway Over the Hudson, Poughkeepsie has many other parks where you can spend some time outside.

Just under the Walkway, you can find Upper Landing Park, which has the seasonal, 21-story, ADA compliance glass elevator to take patrons up so they can experience the Walkway.

College Hill Park is another park in town.

It has the highest point in Poughkeepsie and contains the man-made Morgan Lake, walking trails, and the College Hill Golf Course.

The 1930s paved the way for much of the park’s development.

To honor the site’s history, a building inspired by the Ancient Greek Parthenon was erected in the park’s center.

The grounds served as a school in the 1830s.

A rock garden was also installed. It’s an excellent place for a picnic or as a place to be outside.

Right at the end of Poughkeepsie’s Main Street, you can find Victor C. Waryas Park.

This park has acres of green space right along the Hudson River.

You’ll find walking trails, benches, and a pavilion with picnic tables, along with incredible views of the Walkway overhead.

5. Watch a performance at Bardavon Opera House

The Bardavon is an opera house built in 1869 and is considered New York State’s oldest continually operating theater.

Originally a performance venue, many notable theater performers appeared on its stage until it was renovated for the movie age in 1923.

The theater operated as a cinema from 1923 until 1975, until it was renovated again and added to the National Register of Historic Places.

Today, you can find many different live events, concerts, productions, and performances from the Hudson Valley Philharmonic on its events calendar.

6. Visit the Cunneen-Hackett Arts Center

Interested in art?

The Cunneen-Hackett Arts Center has three galleries featuring art from local and regional artists between its two Victorian-age Italianate buildings.

The Arts Center also offers events and programming for the community.

Contact the Cunneen-Hackett Arts Center for information on current events and hours.

7. Spend a day at the Mid-Hudson Children’s Museum

Adjacent to the Hudson River, the Mid-Hudson Children’s Museum is the only children’s museum in the Hudson Valley between New York City and Albany, the state capital, and is a perfect destination for families with young children to spend a day.

The Museum’s three pillars of focus–school readiness, wellness, and community building–are emphasized with their exhibits on early literacy and STEM learning, as well as arts, health, and its local community.

They have different galleries throughout the space that encourage children to use their developing thinking, feeling, and physical skills.

And if you happen to visit the Mid-Hudson Discovery Museum on a Monday afternoon between June and September, you can’t miss the Poughkeepsie Waterfront Market.

The Museum launched this community farmer’s market in 2017 to bring fresh produce to the community.

8. Enjoy the riverfront at Victor C. Waryas Park

Take a stroll by the Hudson River and admire the view from Victor C. Waryas Park.

Victor C. Waryas Park is a nine-acre park located at the foot of Main Street in Poughkeepsie, adjacent to the Mid-Hudson Discovery Museum.

It offers stunning views of the Mid-Hudson Bridge and features amenities like playgrounds, picnic tables, outdoor grills, a boat launch, a dock, a restaurant, and restroom facilities.

The park also offers something unique: Bridge Music, developed by Joseph Bertolozzi! If you want to listen in, make sure to tune your radio station to 95.3 FM.

Best Things to do near Poughkeepsie

9. Visit the Franklin D. Roosevelt Presidential Library and Museum

Fun Facts about Franklin D. Roosevelt:

• He was the 32nd President of the United States of America
• He was the only U.S. president to serve more than two terms
• He became paralyzed from the waist down after contracting polio
• He was born and raised just outside of Poughkeepsie, in Hyde Park

Only a 15-minute drive from the center of Poughkeepsie, take some time to explore the Franklin D. Roosevelt Presidential Library and Museum and the Eleanor Roosevelt Mansion in the nearby city of Hyde Park.

The farmhouse that the 32nd President of the United States was born in is now a national historic landmark.

Instead of destroying the vast array of papers and documents he had accumulated as president, FDR decided to preserve them.

He raised private funds to develop and build what became the first Presidential Library.

Once completed, FDR gave control of the operation to the United States government, to be overseen by the National Archives and Records Administration – which he signed into existence in 1934.

Now, historians, scholars, and the American public can search through the President’s records and learn for themselves the history within the documents.

Interested in checking out other Presidential Libraries? One of the best things to do near Winchester, Virginia is visit the Woodrow Wilson Presidential Library and Museum!

10. Explore another historic landmark, the Vanderbilt Mansion

Just like their marvelous mansion in Newport, Rhode Island, the Vanderbilt family had their grand estate just outside the bustling little city of Poughkeepsie, in Hyde Park, New York, just down the road from FDR’s.

Designed by New York City architects McKim, Mead & White, the same team that designed iconic buildings like the original Pennsylvania Station, the Morgan Library and Museum, the Brooklyn Museum, and the Manhattan Municipal Building, the mansion was primarily used as a vacation home.

As president, Franklin D. Roosevelt convinced his neighbors to donate part of the historic estates to the National Parks Service.

Today, you can wander the grounds of the Vanderbilt Mansion National Historic Site, walk along designated trails through the now public estate, and take in the view of the river.

11. Go back in time at Historic Huguenot Street

Designated as a National Historic Landmark, Historic Huguenot Street is one of the oldest surviving settlements of its kind in the United States, like Colonial Williamsburg in Williamsburg, Virginia.

The 10-acre district includes a number of buildings from the 1700s and 1800s and explores the area’s enslaved African communities, Native American, and Dutch history.

It’s a great destination for families who are interested in exploring the past for themselves.

Historic Huguenot Street is open for visitors from dusk until dawn, but contact them in advance for information on specific timing and events.

You can download their free walking tour app to guide you through the grounds, or take a guided tour.

12. Drink your day away along one of the wine trails

This area of upstate New York is home to an impressive number of wine trails, including several wineries, restaurants, and bed-and-breakfasts.

The major Hudson Valley wine trail, known as the Shawangunk Wine Trail, is the larger of the two.

There are fifteen wineries on the trail, which is located up in the Shawangunk Mountains.

However, the Dutchess Wine Trail is a great alternative for those looking for a more intimate experience, since it’s focused on three wineries in Dutchess County: Clinton Vineyards, Milea Estate Vineyard, and Millbrook Vineyards & Winery.

They are all located within a 15-minute drive from each other and truly capture the beauty of the area.

13. Take a cruise on the Hudson River

Departing from Kingston, New York, Hudson River Cruises offers sightseeing cruises from Victor C. Waryas Park between May and October aboard the Rip Van Winkle II.

The Rip Van Winkle II is a spacious passenger boat with plenty of seating room and modern amenities to make your journey comfortable and enjoyable.

From May to October, passengers can take in breathtaking views of the river’s natural beauty as they sail past historic sites and landmarks.

Passengers can enjoy sweeping views of charming Hudson River lighthouses, gorgeous riverside mansions, and other incredible local landmarks.

You can check the schedule and book on their website.

14. Bike the Dutchess Rail Trail

The William R. Steinhaus Dutchess Rail Trail is a 13.4-mile paved trail that runs from the Hopewell Depot to the north entrance of the Walkway Over the Hudson.

Open to all walkers and bikers; the trail is part of the larger Empire State Trail. It stretches across the state the way in all four directions, from Manhattan up to the Canadian border, as well as from Buffalo to Albany.

If you want to try biking the trail, you can find City Bike Rentals PK, near the Walkway Over the Hudson, offering bike rentals.

15. End your day at the drive-in

Enjoying a drive-in movie is a classic throwback to the golden age of movie-going.

The Overlook Drive-in and Hyde Park Drive-in are two drive-in theaters found right outside Poughkeepsie.

The theaters offer a double feature starting at dusk (between 8:30 pm and 9:00 pm) and cost just $10 for the two films.

While you can bring your own food and drinks to enjoy while watching the movie from your car or truck, you can also find your favorite treats like popcorn, candy, and soda at the snack bar.

You’ll find the Overlook Drive-In and the Hyde Park Drive-In open seasonally from Friday to Saturday, from dusk until the end of the second movie.

How to Get to Poughkeepsie

When I was looking around the upstate New York area, I wanted a place that was easily accessible by both car and public transportation, and that’s precisely what I found in Poughkeepsie.

Taking a train from NYC to Poughkeepsie is easy!

The small city is the last stop on any trains using the Metro-North Hudson line, making for a just over 2-hour train ride from Grand Central Terminal in Manhattan.

This isn’t a walkable city. To see many of the major museums and points of interest, you’ll either need to rent or drive your own car or take advantage of rideshare apps like Lyft or Uber.

Where to Stay in Poughkeepsie

There are a couple of great hotel options around town!

I recommend the Hyatt Place Poughkeepsie (Booking | Hotels | TripAdvisor) or the Homewood Suites by Hilton Poughkeepsie (Booking | Hotels | TripAdvisor.)

For a luxury stay, just over the Hudson River, you can find Mohonk Mountain House, an all-inclusive resort in the mountains.

Enjoy the resort’s included outdoor activities like guided tours, outdoor adventure and traditional sports, activities for kids, and entertainment every night, while enjoying farm-to-table dishes for every meal.

This is a great option if you really want truly romantic getaways and are only planning to explore a few of the sites in the area or want to take advantage of the resort’s activities as a day guest.

Where to Eat in Poughkeepsie

With the premier Culinary Institute of America in the next town over, Poughkeepsie has some phenomenal restaurants.

Thomas Kacherski, the creator of the restaurant Crew, is a CIA graduate who established his trendy spot near his alma mater.

Brasserie 292 or Cosimo’s are two other great restaurants for a cute date night out.

If you’re looking for a quick bite, Rossi & Sons Rosticceria is the best deli in town.

There are also several breweries around, like Mill House Brewing Company, or Blue Collar Brewery.

Head over to one of these bars for the night, or even create your own pub crawl if you’re looking for other things to do in Poughkeepsie.

If you’re interested in waterfront spots, Ice House on the Hudson is a casual summertime seafood restaurant, right on the Hudson River.

Or, head to Shadows on the Hudson for a fine dining experience, with both indoor and outdoor seating choices.

Day Trips from Poughkeepsie

New York City

If you’ve never been to New York City, this is a great opportunity to go!

Poughkeepsie is a less than two-hour train ride away from the Big Apple, making it a great day trip.

Read up on my guides to navigating the subway, the best observatories, free activities, and free museum hours for some tips and ideas.

New Haven, Connecticut

If you’ve rented a car for this trip, and want to get out to see another part of the Northeast, try heading East into Connecticut!

The “Elm City” is an easy day road trip from this Hudson riverfront town.

You’ll find in my guide of things to do in New Haven that Yale University is the heart of the city, and the home of apizza, which ranks over and over again as the best pizza in the United States!

The city also has some of the best breweries in Connecticut.

What are your favorite things to do in Poughkeepsie?

Get your list of Free Activities in New York City

I’m sure you’ve heard the phrase – the best things in life are free. Why not begin your adventures with this book of the best free activities in New York City!