A Hudson Valley Getaway Guide: 16 Delightful Things to Do in Dutchess County

Since I live in Brooklyn, the Hudson Valley has been one of my favorite areas to visit for a long while now! It’s so easy to plan a short escape here from the city, and I especially love going towards the center in Dutchess County! There are so many fun things to do here, you could keep coming back season and season and still find more to experience!

Below are some of my best recommendations to help you plan your own trip.

Watch my Dutchess County episode below:

A Dutchess County Travel Guide

Where is Dutchess County?

If you look at a map of Hudson Valley, you’ll notice there are ten counties equally split on each side of the Hudson River. Dutchess County is right in the middle on the east side with Columbia County to the north and Putnam County to the south. If you were driving from midtown Manhattan, it’d be just under 2 hours to get to its main town, Poughkeepsie. 

Fun Fact: The name “Dutchess” comes from Mary of Modena, the Duchess of York! Spelling it with a “t” is an old spelling.

Best Time to Visit

Personally, I think there’s charm to Hudson Valley no matter the season! But if you do want to travel on the quieter side, I should note there are a few colleges in Dutchess County, so you’ll want to avoid move-in weekend and graduation weekend! 

Where to Stay

You can really stay wherever in Dutchess County since the furthest distance you’ll go is a little over an hour driving. To be more central, check out hotels in Hyde Park or Poughkeepsie. We based ourselves at Hyatt Place Poughkeepsie during filming.

Have Some Cash on Hand!

And as always just a note to take out some extra cash. You’ll want some for hotel tips but also in case you come across smaller farm stands or shops that take cash only.

16 Delightful Things to Do in Dutchess County

1. Check out Destination Dutchess’s Finder Trails

If you just want something easy to follow while you’re in Dutchess County, I really love their tourism board’s Finder Trails. It’s a mobile passport program that has a number of themed trails whether you want to find zen in the outdoors, learn more about the county’s history, or find all the best dessert stops! 

2. Take Time to Explore All the Small Towns

Part of the charm of Hudson Valley as a whole is how many small towns flourish here. Think downtowns straight out of a storybook, small businesses and restaurants, and, of course, there’s usually a good coffee spot all the locals hang out in! When you visit Dutchess County, give yourself time to explore these towns. Poughkeepsie is the big one to check out, but be sure to look into others like Millerton or Beacon.

3. Get Moving Outside

I mean the top reason Hudson Valley is such a lovely escape from the city is all its beautiful outdoors! There are truly so many ways to get moving outside in Dutchess County alone, make a plan to do at least one of them! Some ideas:

• Harlem Valley Rail Trail – this 26-mile paved trail goes through both Dutchess and Columbia counties and is great for those who love biking. Just imagine – cycling without having to stop at every block!!
• Mount Beacon Park – a short but steep mile-long hike for really incredible views of the Hudson River 
• Poet’s Walk – a two-mile walk in Red Hook that’s designed as a series of “outdoor rooms,” and one of the loveliest scenic walks in Hudson Valley. They say Washington Irving came up with “Rip Van Winkle” while roaming around here.
• Brace Mountain – for those that like to get to the highest point in a hike, Brace Mountain is the highest in Dutchess County at 2,311ft. The trail to get there is around 3.6-miles out and back from Millerton.
• Kayaking on the Hudson – there are five different places in Dutchess County where you can rent a kayak – Scenic Hudson’s Long Dock Park, Quiet Cove Riverfront Park, Hyde Park Landing, Norrie Boat Basin, and Tivoli Bays. When the weather is nice, you can kayak along the river and see a number of historic landmarks along the shore.

4. Walk over the Hudson River

If you’re not really interested in breaking a sweat, I’d encourage you to at least check out the Walkway Over the Hudson. It was once a railroad bridge that connected Poughkeepsie and Highland and was constructed in 1889. As cars became more and more popular, it fell out of use and was closed down permanently after a fire in 1974.

Fast forward about 40 years and a group of friends decided to save the bridge and turn it into a pedestrian walkway! It’s now become the world’s longest elevated pedestrian bridge with a path that stretches about 1.28 miles and is part of the Hudson Valley Rail Trail. You can stroll across and take in the gorgeous views of the Hudson River right in the middle of it.

5. Enjoy the Beautiful Innisfree Garden

When it comes to scenic Hudson Valley walks, I have to say the Innisfree Garden might just be my favorite. Situated on 150 acres overlooking Tyrrel Lake, the garden gets its name from “The Lake Isle of Innisfree,” a Yeats poem that describes a longing for an idyllic, peaceful escape while stuck in a city. Pretty fitting for a garden less than two hours away from one of the busiest cities in the world!

The garden began in the 1920s when Walter and Marion Burt Beck began work on their country residence. Walter was heavily inspired by Asian art, especially by an 8th century Chinese artist, Wang Wei, and his famous garden at Wangchuan Villa.

The Becks enlisted help from Lester Collins, a landscape architect who would travel through Asia and even spend a year in Japan studying traditional garden design. Together, the three of them built Innisfree Garden over the course of their lifetimes, leaving it to the public when Collins passed away. The grounds are absolutely breathtaking, so take your time wandering through.

6. Enjoy the Dutchess County Fairgrounds

Located in Rhinebeck, who doesn’t love a county fair? Around since 1841, not only do the Dutchess County Fairgrounds host an annual fair each August, they have a ton of events all year round. Come in May for their antique shows. June hosts the Rhinebeck Crafts Festival while September hosts the Hudson Valley Wine & Food Fest. October is a particularly fun month as you can visit Handcrafted Octoberfest one weekend and then go for the NYS Sheep & Wool Family Festival the next. (Just ask any knitter you know about that last one, and they’ll likely be familiar!) 

7. Visit the Home of One of Our Greatest Presidents…

No visit to the area is complete without stopping by the Home of Franklin D. Roosevelt National Historic Site, also known as Springwood Estate. F.D.R. has the distinction of being the only president to serve more than two terms, and it’s his leadership through the Great Depression and World War II that has made him such a significant name in the history books. After all, this is the president that gave us, “The only thing we have to fear is fear itself.”

President Roosevelt was born in Springwood, and he would eventually move in with his new wife after his father passed. Even as he rose to political prominence and became president, he often returned here and eventually established the country’s first ever presidential library in 1939.

Today, you can visit the library and museum to learn more about Roosevelt’s work and influence. 

As a bonus, you can also visit Top Cottage to see where he liked to escape for some peace and quiet.

8. …And then Visit Eleanor Roosevelt’s Personal Retreat

While you’re visiting Springwood, take time to visit the Eleanor Roosevelt National Historic Site. Another distinction of F.D.R.’s presidency is that his wife left an equally significant mark on history. Many of us know Eleanor Roosevelt’s name and remember studying the impact she had as the longest serving First Lady, changing the nature of the role altogether. Not only did she step up in times her husband’s polio held him back, she was an advocate for a wide range of human rights issues well before they were popular.

On the same grounds only two miles away sits what was once her personal retreat and is now a museum in her honor. Named Val-Kill, its unusual shape is because it was once a furniture factory. After the president died in 1945, she moved here full time and often hosted a huge range of guests. It’s the first national historic site to be dedicated to a First Lady,  and it’s free to visit. Start your trip at the Stone Cottage Visitor Center to check out more of the cottage’s history.

If you really want to stretch your legs, you can also walk between Springwood and Val-Kill along the 1.8-mile Farm Lane Trail.

9. Dine at the Culinary Institute of America

When it comes to eating in Dutchess County, you’re in for a treat as it’s home to one of the most distinguished culinary schools in the world – the Culinary Institute of America. As with most similar establishments, the C.I.A has a teaching restaurant which allows students to get some real world experience while visitors get to experience gourmet fine dining from some future James Beard winners at a fraction of the cost.

The Bocuse Restaurant is located in Hyde Park and named after famous French chef, Paul Bocuse. Its focus is on classic French cuisine but with modern techniques in a casual yet sophisticated atmosphere. Be sure to make reservations ahead of time, and if you’re curious, you can also book an afternoon tour to the C.I.A. as well.

10. Check Out Homes from the Gilded Age

Considering Hudson Valley has been a favored escape from New York City for decades, it’s no wonder some of the Gilded Age families came here as well. There are two notable spots you can visit in Dutchess County: 

• Staatsburgh State Historic Site – Also known as Mills Mansion, this mansion was home to Ogden Mills and Ruth Livingston Mills. What makes it unique is that they took the Greek-Revival style home and did a Beaux-Arts renovation so that it’s a mixture of both styles.
• Vanderbilt Mansion National Historic Site – This Vanderbilt mansion actually shares its name with the town, Hyde Park. It’s as grand as you’d expect from the Vanderbilts with a Beaux-Arts architecture style and an American Renaissance interior. Frederick and Louise Vanderbilt used it as a vacation home and it was their niece who donated it to the National Park Service (as encouraged by her neighbor, FDR!) Fun Fact: his secret service was housed here from 1941-43.

11. Check out the Exhibits at Barrett Art Center

There are a lot of fantastic places for art lovers to go around Dutchess County, but if I had to pick one, it’d be the Barrett Art Center in Poughkeepsie. Located in a Greek Revival brick townhouse in a residential neighborhood, its aim is to foster a love of visual arts in Hudson Valley. The name comes from Thomas Weeks Barrett, Jr, who once called the center his childhood home and helped found the Dutchess County Art Association.

Check their website for current exhibitions. One of the best things about the center is that entrance is free to ensure that there are no financial barriers to anyone who wants to visit.

12. Catch a Movie at an Old School Drive-in Theater

Believe it or not, there’s not just one but two places to enjoy a movie from your car the old fashioned way! The first is at the Four Brothers Drive-In Theatre in Amenia and the second is at the Overlook Drive-in Theater in Poughkeepsie. 

13. Visit an Abandoned Castle

One of the most unique things to do in Dutchess County is to visit an abandoned castle – yes, you read that correctly! Located on the tiny Pollepel Island sits Bannerman’s Castle. Unfortunately, there is no fantastical explanation for why there’s a castle in the middle of the Hudson River. Back in 1900, Francis Bannerman VI bought the island to use as a storage facility for his army surplus business. Based on Scottish castle designs, he designed the castle to be a huge advertisement as it’s easily visible from the land.

Today, the castle lies abandoned and in ruins after a fire destroyed most of the facilities in the mid-1900s, giving it a spooky, haunted atmosphere. To get to the castle today, you can book a cruise and walking tour or kayak over yourself.

14. Tour the Oldest House in Dutchess County

Right in Beacon, the Madam Brett Homestead pre-dates the United States by 67 years! It was built in 1709 by Roger and Catheryna Brett and stayed within the family for seven generations! You can book a tour to visit and learn about all its history!

15. Try Your Hand at Some Clay Shooting

Looking to try your hand at some shotgun shooting? Check out the Sandanona Shooting Grounds in Millbrook. It is the oldest permitted shooting preserve in the United States, starting all the way back during Thomas Jefferson’s presidency. With over 200 years of practice, you know they know how to work with all sorts of visitors, especially total beginners.

When you visit, be prepared – shooting is a sport, after all. The grounds span 400 acres with 20 stands. Sandonona doesn’t create any artificial land, either. They’ve built their courses to work with the natural landscape. Choose between two different courses and spend your non-shooting time relaxing on their wrap-around porch. And don’t worry – no animals will be harmed during your excursion. Clay shooting means you’re shooting at clay objects.

16. Sample from over 300 Teas at Harney & Sons

When it comes to tea, Harney & Sons is the gold standard. Over four decades ago, John Harney decided to turn his passion for fine tea into its own business. What started as experimenting with new blends in his basement is now a recognizable Fair Trade Certified™ brand found in boutiques all over the world with over 300+ flavors from which to choose.

As a tea aficionado who even travels with her own cup, I knew I had to visit their flagship location in Millerton. It also has a food menu, so it’s a perfect place to stop for lunch and relax for the afternoon with a steaming cup of tea (or two or three, I won’t judge!).

And there are some of my top recommendations for things to do in Dutchess County. From the outdoors to culture and history to fantastic eating and drinking, you might just think of moving out of the city for this place!