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???

COVID-19 NOTICE

Although some of these locations are open to the public, please follow these guidelines:
Please be safe.
Practice social distancing, wear a mask, wash hands thoroughly and follow all mandates and recommendations of the Centers for Disease Control (cdc.gov) and NY State and local Governments.

Visiting the FDR National Historic Site is one of the best things to do in Dutchess County

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.
  • Because of the pandemic, many Dutchess County events have been cancelled. Make sure to confirm information 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?


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. This is one the best family things to do in the Hudson Valley.
Dutchess Stadium

According to dutchesstourism.com:

“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

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.

DIA:Beacon

OPEN to the public with reservation

  • 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

OPEN to the public on Sat & Sun only

  • 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.
One way to get to Bannerman Castle is by taking a ferry from Beacon, NY. Dutchess County, NY residents and visitors all awe at the beauty of this structure. This is one of the great and adventurous things to do in Dutchess County.
Bannerman Castle, Hudson River

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.

Hudson Valley Farmers Markets

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 Beach Glass, Beacon, NY is a very cool place. Where else can you blow your own glass ornament. Oh, wait .. there is another place in Dutchess County, NY
Hudson Beach Glass, Beacon, NY

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.


Historical Places in Dutchess County


Springwood in Hyde Park is one of the Hudson Valley Landmarks important in history. If you like history then this is one of the wonderful things to do in Dutchess County.

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.

Although tours were suspended in 2020, the grounds of many of these historic sites are open year-round for your enjoyment.

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


First Friday Poughkeepsie

Although suspended for 2020, Poughkeepsie’s First Friday Events are the best thing to happen to Poughkeepsie. Six events take place on six different days, with six different themes in six different locations.

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.

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
First Friday Poughkeepsie is a

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 entrance to the Dutchess County Fairgrounds in Rhinebeck, NY

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!


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.

How to Plan a Day, Weekend, or Week of Things to do in Dutchess County:

I know that making plans and itineraries can be tough and overwhelming, especially with so many things to do in Dutchess County.

Itineraries are the best way to plan your day anywhere. It doesn’t have to be anything fancy. Some people prefer making lists behind envelopes or scraps of paper. Some people, like me, like to plan things out online.

I believe so much in itineraries that I created a product to make it easier for you to see more and do more in parts of the Hudson Valley. It’s called, Quick & Easy Itineraries for Hudson Valley Explorer and I’ve literally made 10 ‘Done For You’ Itineraries that are a great starting point.

Quick & Easy Itineraries for the Hudson Valley Explorer

Above is a quick little preview of the itineraries that you’ll get. Get the Quick & Easy Itineraries Here.

Tips For a Successful Day at Any Dutchess County Location

  • Many things to do in Dutchess County require reservations. Check information online before visiting the locations/
  • Confirm all information with the locations before making definite plans.
  • Weather conditions may change drastically, so confirm the weather before making plans. I use the AccuWeather app everyday before I head out the door.
  • Many locations are open seasonally. Check each individual location for the days/times they are open to the public.

Where to Next???

Now that you have information regarding Dutchess County, let’s see where you should go next…

Map Key for the Hudson Valley Exploring Map

Until the Next Adventure…

PIN IT FOR LATER!

A Quick Guide to 'Almost' Everything in Dutchess County, NY. There is so much to do that one blog post does not do it justice.
List of Free Things to do in the Hudson Valley

Jackie from Hudson Valley Exposed

Jacqueline Ramirez

Jackie is one of the top bloggers in the Hudson Valley. A solo entrepreneur, she has been featured (along with some of her photos) in several publications, locally and nationwide. Read Jackie’s crazy story, “From a Naive NYC Girl to Popular Hudson Valley Blogger & Author“. Feel free to send Jackie a message here.