Things to do in Dutchess County

19+ Fun Things to do in Dutchess County (That you Should Keep Secret)

Did you know that there are an abundance of things to do in Dutchess County? The list is so long, there is no way

Believe me when I tell you that there are so many things to do and see in Dutchess County, NY, that I could not list them all in this blog post. Crazy… Right???

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Things to know before finding things to do in Dutchess County:

  • Dutchess County is a large county. If you’re spending the day in lower Dutchess, you will probably not have enough time to do things in upper Dutchess County.
  • Information changes quickly. Make sure to confirm information with each location and organization before making plans.
  • Several highways run through Dutchess County and make it a little easier to get from one area to another.

Where is Dutchess County, NY?

Map of Dutchess County NY
Courtesy of Wikipedia

Dutchess County, NY sits along the Hudson River and is sandwiched between Columbia County and Putnam County, with Orange County bordering it on the other side of the Hudson River.

It is also located between the Hudson River and the state of Connecticut.

With just over 800 square miles, there is plenty to do in Dutchess County. From farmlands to small cities, Dutchess County is full of open spaces, bustling towns and the arts.

Some places that you may already know in Dutchess County include: Poughkeepsie, Rhinebeck, Beacon, and Fishkill.

Dutchess Stadium is the best family fun you can have during the summer. Located in Dutchess County, NY, they provide themed evenings for their games.
Dutchess Stadium

According to

“Covering 800 square miles, there’s an abundance of natural scenic beauty, outdoor recreation, historic landmarks, restaurants, festivals and more.”

Cities & Towns in Dutchess County NY

Dutchess County is a distance of 58 to 110 miles from New York City, depending on where you are visiting in Dutchess County.

  • Amenia
  • Beacon
  • Beekman
  • Clinton
  • Dover
  • East Fishkill
  • Fishkill
  • Hyde Park
  • LaGrange
  • Milan
  • Millbrook
  • Millerton
  • North East
  • Pawling
  • Pine Plains
  • Pleasant Valley
  • Poughkeepsie
  • Red Hook
  • Rhinebeck
  • Smithfield
  • Stanford
  • Tivoli
  • Union Vale
  • Wappinger
  • Wappingers Falls
  • Washington

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How do you get to Dutchess County, NY?

If you’re in New York City, you can hop on the Metro-North Hudson Line or Harlem Line and several bus companies. These transportation methods can take you either end of Dutchess County without a hitch.

  • The Hudson Line takes you from Grand Central Station in NYC directly to Poughkeepsie, NY with a stop at Beacon, NY.
  • The Harlem Line takes you from Grand Central Station in NYC on the Eastern part of Dutchess County with stops in Pawling, Wingdale, Dover Plains, etc.

By car, major highways in and around Dutchess County include:

  • I-84 (East/Westbound), 
  • Taconic State Parkway (North/Southbound),
  • US Route 9 (North/Southbound)
  • NY Route 22 (North/Southbound)

Don’t forget to find a way of crossing the Mid-Hudson Bridge and the Kingston – Rhinecliff Bridge while you’re out exploring. The views of the Hudson River from these two bridges is amazing!

The view of the Mid-Hudson Bridge from the Ulster County parking lot. Walking across the bridge is one of the fun things to do in the Hudson Valley.
Mid-Hudson Bridge

Highlights of Things to do in Dutchess County:

To be honest, I am always in awe by all the things to do in Dutchess County. I have a very long ‘Wish List’ of things I want to do in Dutchess County and get excited about all the exploring I have ahead of me.

What are some things to do in Dutchess County?

The Arts in Dutchess County

Exhibits and people walking at the DIA:Beacon. Visiting art museums is a great thing to do in the Hudson Valley.


  • If you love art, a visit to DIA:Beacon is a must. Located next to the Metro-North Beacon station and Route 9D, DIA: Beacon is conveniently located and easily accessible. The vast amount and variety of art is amazing.

Francis Lehman Loeb Art Center

  • The Francis Lehman Loeb Art Center is located on the campus of Vassar College campus in Poughkeepsie. The collection consists of paintings, sculptures, drawings, prints, photographs, textiles, and glass and ceramic wares.
Visitors to Katonah Museum of Art

Farmers Markets in Dutchess County

During the Summer, some of the best Farmers Markets take place in Dutchess County. Some of these markets are also open during the winter. They encourage a sense of community while showcasing the best of Hudson Valley products and produce.

If you’re struggling to find some markets near you, curious about where markets are located or if you’re looking for a new farmers market to visit, you can always look at my comprehensive list: The Ultimate List of Hudson Valley Farmers’ Markets. This article showcases all Hudson Valley Farmers Markets, both in the summer and year-round.

Vegetables at a Hudson Valley Farmers Market.

Glass Art in Dutchess County

Dutchess County is home to premier Glass Blowing Studios. Take a trip to these unique places and watch a demonstration and/or try your hands on blowing some of your own glass.

Hudson Beach Glass

Hudson Beach Glass in Beacon, NY is a popular place to visit. Although in-person glass blowing was suspended for 2020, this is typically the main attraction at this great gallery and studio.

Hudson Valley EXposed

Farms in Dutchess County

Dutchess County has an extensive selection of farms. These places are great for a family fun – filled day of picking your own fruit. It doesn’t matter if it’s in the summer or fall, Dutchess County has the best farms around.
The busiest season is Apple-picking Season.

Have you ever thought about cutting down your own Christmas Tree? You can do so in Dutchess County.

Historic Places in Dutchess County

Springwood in Hyde Park is one of the Hudson Valley Landmarks important in history

One of the most influential people to live in Dutchess County where ‘The Roosevelts’.

Hyde Park, NY is home to the Franklin D Roosevelt Home National Historical Site, Franklin D Roosevelt Presidential Library and Museum and the Eleanor Roosevelt National Historic Site.

The grounds of many of these historic sites are open year-round for your enjoyment and some locations are offering tours once again.

In addition to these wonderful places, other historical places in Dutchess County include:

Mount Gulian Historic site is a very special place in Dutchess County, NY. They host many events for young and old.
Mount Gulian Historic Site

Performing Arts in Dutchess County

Many Dutchess County music venues and performing arts centers had to cancel productions and performances for the 2020 Season.

In addition to music and other live events that often take place at the Mid-Hudson Civic Center, other notable places to see performances around Dutchess County are:

Sports in Dutchess County

But, did you know that Dutchess County, NY is home to a sports teams? The Hudson Valley Renegades play baseball at Dutchess Stadium in Fishkill. How cool is that?!?

In addition the Sports Museum of Dutchess County is located in Wappingers Falls. Open seasonally, the “Legends of Dutchess” tells the history of different sports and athletes from Dutchess County.

Events in Dutchess County

Second Saturday Beacon

Beacon’s Second Saturday is the highlight of every month. Second Saturday Beacon is a city-wide celebration of the arts held on the second Saturday of every month when galleries and shops stay open until 9pm. Gallery openings, music are just some of the ongoing events.

Find out why Beacon is a favorite of Many!

Poughkeepsie, NY shows off its community through the First Fridays events that happen throughout the year. Dutchess County, NY is lucky to have this wonderful event.
First Friday in Poughkeepsie, NY
Hudson Valley Summer Activities

Dutchess County Fair

And, let me tell you… the Dutchess County Fair is a pretty awesome Fair.

In addition to their famous Summer fair, the Dutchess County Fairgrounds is also home to several unique events:

  • Rhinebeck Antique Car Show & Swap Meet
  • The Rhinebeck Crafts Festival
  • Hudson Valley Hot Air Balloon Festival
  • Hudson Valley Wine & Food Fest
  • Rhinebeck New York Cider Festival
  • NYS Sheep & Wool festival
The Dutchess County, NY Fairgrounds hosts wonderful events throughout the year, including the Dutchess County Fair.

What are some things to do in Dutchess County today?

In addition to my Hudson Valley Events FB Group, the Events Calendar at the Dutchess County Tourism website is full of events taking place within the County. It is one of the most comprehensive County Events Calendars around!

If you’re looking for FREE Things to do in Dutchess County, then this article is for you.

What are some things to do in Dutchess County this weekend?

With so many things to see and do in Dutchess County, NY, it may take you some time to get through them all. But something I can guarantee is that you may WILL have fun doing so.

Don’t forget to click the tab above for ‘Dutchess’ and this will direct you to all the blog posts written about places in Dutchess County.

Unique Outdoor Spaces in Dutchess County

There are no shortage of outdoor spaces in Dutchess County, but there are certainly unique things to do in Dutchess County that you can do most days & weekends.

  • Walkway Over the Hudson State Historic Park (open year-round, weather-permitting) – The world’s longest pedestrian walkway allows you to walk over the Hudson River from Poughkeepsie, NY to Highland, NY (Ulster County). The views from The Walkway are spectacular and they often host events.
  • Bridge Music at the Mid-Hudson Bridge (open seasonally) – This unique musical experience combines breath-taking views of the Hudson River and Hudson Valley along with the music made by Joseph Bertolozzi while using the bridge as an instrument.

Tips for a Successful Day at any Dutchess County Location:

  • Many things to do in Dutchess County requires a reservation.
  • Confirm all information with the locations before making definite plans.
  • Weather conditions may change drastically, so confirm the weather before making your plans. I use the AccuWeather App everyday before I head out the door.
  • Many locations are open seasonally. Confirm each locations days/times of operation.

Find More Things to do in the Hudson Valley Here:

These Hudson Valley Attractions are Perfect for a day or weekend out

The Ultimate List of Free Things to do in the Hudson Valley

Hudson Valley Castles that seem to be from another country

Until the Next Adventure…

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