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19 Fun Things to do around Poughkeepsie on a One Week Workcation

Looking for things to do in Poughkeepsie? Discover things to do around Poughkeepsie. Find the best attractions near Poughkeepsie NY on a workcation.

Upstate New York is a great place for a workcation. 

What's a workcation, you may ask? A workcation is a trip where (if your job allows) you bring your laptop and work from a new location. 

Workcations provide a change of scenery and an opportunity to experience what it's like to live in a different place for a short period of time. 

We discovered a variety of fun things to do around Poughkeepsie that we wouldn't have seen had we not embarked on a workcation adventure. Work during the day but use the mornings, lunchtime, evenings, and weekends to make the most of your destination.

View of Poughkeepsie from the Walkway over the Hudson

Getting to Poughkeepsie

Poughkeepsie is located in the Hudson River Valley less than a 2 hour drive from Newark Airport. Similarly, it takes about 90 minutes to reach Poughkeepsie from New York City by car and about 2 hours by train from Grand Central Station. 

We flew in and out of Newark Airport and spent a one week workcation in Poughkeepsie after a road trip to Buffalo (home of amazing architecture and famous foods in Western New York). It takes around 6 hours to drive from Buffalo to Poughkeepsie.
River of the New York City Skyline across the Hudson River.

Where to Stay in Poughkeepsie

We chose to stay in Poughkeepsie rather than in a smaller quaint town in the Hudson River Valley for a few reasons:
  1. Poughkeepsie is centrally located in the Hudson Valley with many points of interest within an hour's drive north or south.
  2. There are a number of larger hotel chains in Poughkeepsie. We stayed at the Residence Inn by Marriott Poughkeepsie to avail of the larger suites and a comfortable desk which is so important for a workcation!
  3. The hotels in Poughkeepsie were cheaper than in many other Hudson River Valley towns. The Residence Inn cost $139 USD per night for our stay.
SIDEWALK SAFARI SPOTLIGHT: Looking for other weekend getaway or workcation ideas in New York State? Why not go leaf-peeping and discover all the cool things to do in Saratoga Springs or visit the land of concord grapes in Westfield New York.

Things to do around Poughkeepsie at a Glance

Let's get an overview of things to do in and around Poughkeepsie to help you figure out if a workcation in the Hudson River Valley is ideal for you.

Fall foliage and Mid-Hudson Bridge viewed from the Walkway over the Hudson
  1. Explore Roadside Views of the Hudson River
  2. Go Leaf Peeping
  3. Eat Top Notch Bagels
  4. Try New York State Craft Beers
  5. Take a Self-Guided Tour of Vassar
  6. Explore New Paltz on a Morning Walk
  7. Visit Revolutionary Beacon, NY
  8. Take a Guided Tour of Vanderbilt Mansion
  9. Hike the Walkway Over the Hudson State Historic Park
  10. Tour FDR Library
  11. Enjoy an Art Deco Lunch at Eveready Diner
  12. Make a Pitstop at Mills Mansion
  13. Shop Rhinebeck 
  14. Admire Saugerties Architecture
  15. Unleash Your Inner Hippie in Woodstock
  16. Check out the West Point Museum
  17. Seeking the Facts of Life in Peekskill
  18. Experience the Legend of Sleepy Hollow
  19. Go For a Photowalk in Cold Spring

Map of Things to do Around Poughkeepsie

The various attractions near Poughkeepsie, NY are most easily visited with a car. Click on the image of the map below to open up an interactive version in Google Maps to help you plan your drives in the Hudson River Valley.

Map of things to do around Poughkeepsie

Things to do around Poughkeepsie during a Workcation Week

Now let's explore the things to do around Poughkeepsie in detail. In general, I shifted my workday to start and end a little later so that we could take a drive for coffee and a walk in the morning. 

Let's start by exploring places near Poughkeepsie that are easy to blend into a workday. 

1. Explore Roadside Views of the Hudson River

We stopped at a lovely viewpoint in the Hudson River Valley en route to Upstate New York. There were a bunch of birders buzzing around State Line viewpoint. 

It turns out that there was a Peregrine Falcon perched almost within arms reach! I wish I'd brought my good camera on this trip. My phone did a pretty good job though!

State Line Viewpoint on the Hudson River en route to PoughkeepsiePeregrine Falcon at State Line Viewpoint

2. Go Leaf Peeping

Depending on how you time your drive from New York City to Poughkeepsie, you may encounter slow traffic. I tried to put a positive spin on stop and go traffic. It meant that we had the opportunity to admire the Fall foliage from the comfort of our car. 

Definitely make time to stop and admire the Fall colors if you time your Poughkeepsie workcation for the Autumn like we did.
Fall Foliage en route to Poughkeepsie NY

3. Eat Top Notch Bagels

One thing that I really miss about living in New York State is the hot, delicious bagels. 

We stopped in Nyack and enjoyed a yummy cracked pepper turkey bagel. There is nothing finer than a fresh bagel sandwich as a pitstop on a road trip.
Bagel Sandwich in Nyack New York

4. Try New York State Craft Beers

Another great reason to stay in a suite hotel is that you can avail of a full size refrigerator. We stocked up on some great New York State craft beers. We toasted our arrival in Poughkeepsie by kicking back with a Northway Brewing Session IPA. 

Definitely make time to sample some of the craft beers that are local to Poughkeepsie. We ate dinner at Mill House Brewing Company. 

We were treated to huge portions of kielbasa and pierogies plus meatloaf which paired well with a tasting platter of house brewed beers. Between us we tried 10 of the 16 beers on the menu. Cross Reference raspberry sour was my favorite! Cucumber Blessings tasted like spa water.
Things to do in Poughkeepsie: beer tasting at Mill House Brewing CompanyThings to do Around Poughkeepsie: drink craft beer at Kingston Standard BrewingPizza at Kingston Standard Brewing in the Hudson River Valley
We also managed to squeeze in a visit to Kingston Standard Brewing in Kingston, NY during our Poughkeepsie workcation. We drank an amazing sour IPA and ate a fresh margarita pizza at the picnic tables outside the brewery. Yum!

5. Take a Self-Guided Tour of Vassar

One of the most fun things to do around Poughkeepsie that we discovered on our workcation was a self-guided tour of Vassar College. Vassar is a prestigious private liberal arts college. 

Vassar College was founded in 1861 and was just the second degree-granting institution of higher education for women in the U.S. at that time. Vassar went co-ed after declining an invitation to merge with Yale in 1969. 
View from the library at Vassar College in PoughkeepsieDoor to the dining hall at Vassar College in Poughkeepsie NY

We parked at a meter and grabbed a coffee at Crafted Kup which is within walking distance of campus. Armed with caffeine, we then embarked on a lovely walk around the Vassar campus. 

The library was open so we walked right in. We discovered a classic college atmosphere and neat historic architecture. 

You'll also find some excellent shots for your Instagram feed on Vassar's picturesque campus. I particularly loved the impressive entrance to the main dining hall.
Things to do in Poughkeepsie: Take a walk on Vassar College Campus

6. Explore New Paltz on a Morning Walk

One morning we took a drive from Poughkeepsie to New Paltz (about 30 minutes by car north and across the Hudson River). The views from the Mid-Hudson bridge are stunning in the morning light. 

We enjoyed a quick atmospheric stroll in New Paltz before sitting down at my laptop to continue our Hudson River Valley workcation.
Mitzvah Wall at La Gusta's Luscious Commissary in New Paltz New YorkMitzvah Wall at La Gusta's Luscious Commissary in New Paltz New York

We grabbed a vegan pumpkin latte and artisanal caramels flavored with apple from La Gusta's Luscious at La Gusta's Luscious Commissary in New Paltz. The place has a great vibe. The Mitzvah board where people can buy a coffee for someone really touched my heart.

We finished our workcation adventure in New Paltz by taking an early morning walk down Huguenot Street. We were surprised by the amount of history tied to New Paltz.  Six stone houses date back to the 17th century.
Things to do around Poughkeepsie: Huguenot Street in New Paltz

7. Visit Revolutionary Beacon, NY

We continued our pace of exploring things to do around Poughkeepsie and headed south this time. We went for a drive and then a morning walk in Beacon, NY. 

This village on the Hudson is named for the beacons that George Washington placed in the area during the Revolutionary War so there is a rich history associated with the town.
Big Mouth Coffee in Beacon NYThings to do around Poughkeepsie: Beacon, NY
The first port of call on any workcation adventure is a stop for coffee. We tried Big Mouth Coffee in Beacon. I loved the atmosphere. Get your lid from atop a vintage stove.

Beacon extends several blocks along Main Street so we did a loop of the town: out on one side of the sidewalk and back on the other. We heard burbling water and went to have a look at Fishkill Creek. So idyllic and made even more so thanks to gorgeous Fall colors!

Beacon features sturdy brick architecture and repurposed factories and is ideal for a photowalk. Beacon also has its fair share of picturesque doors which for me is always a plus.
Places to visit in the Hudson River Valley: Greetings from Beacon Sign
What's better than the first coffee of the day? Second coffee! 

This time we tried Bank Square Coffeehouse. We took time to eat breakfast al fresco on a chilly November morning at Beacon Bread Company. 

Turkey bacon, egg, and cheddar on brioche plus an indulgent sticky cinnamon bun in itself made the drive to Beacon worthwhile.
Sticky Cinnamon Bun from Beacon Bread Company in Upstate NYEgg Sandwich from Beacon Bread Company in Upstate NY
We finished our morning workcation outing in Beacon with a visit to Scenic Hudson's Long Dock Park. 
I loved the mist rising off the Hudson and views of Newburgh across the river. We found plenty of free parking which was wide open early morning on a weekday.
Mist rising from the Hudson River in Beacon NY

8. Take a Guided Tour of Vanderbilt Mansion

Explore the grounds of the Vanderbilt Mansion in Hyde Park, NY and behold the Gilded Age opulence! 
Things to do around Poughkeepsie: Vanderbilt Mansion in Hyde Park New YorkThings to do around Poughkeepsie: Inside Vanderbilt Mansion in Hyde Park New York
We booked ourselves in for a guided tour of Vanderbilt Mansion. Super knowledgeable guide, Dmitri, from the National Park Service showed us around. 

It was like being transported back to the turn of the 20th century in the Hudson River Valley during the Gilded Age and the reign of the so-called Robber Barons.

Poughkeepsie Day Trips: North to Woodstock

We also made the most of our weekend days in Poughkeepsie to see a lot in a short period of time. I took a day off from work at the end of our Hudson Valley workcation so that we'd have more time to explore the things to do around Poughkeepsie and all that the Hudson River Valley has to offer. 

Let's discover things to do around Poughkeepsie on a drive north to Woodstock.

9. Hike the Walkway Over the Hudson State Historic Park

Attractions near Poughkeepsie NY: Walkway over the Hudson
First stop? Walkway Over the Hudson, the world's longest elevated pedestrian bridge. 

Pay $7 to park by the east trailhead. Allow at least 90 minutes for the round trip walk over the bridge and back. 

There are train tracks that run alongside the river and we even saw a freight train go by reflected in the water which made for a surprisingly picturesque composition.  You'll definitely want to stop and take pictures.
Walkway over the Hudson: Train reflected in the Hudson River

10. Tour FDR Library

Busts and a piece of the Berlin Wall outside the FDR Library in Hyde Park, NY
We continued on from the Walkway over the Hudson to the FDR Library in Hyde Park for a timed entry self-guided tour. Prebook to avoid disappointment. 

The Roosevelt Library (FDR was the first to start a tradition of presidents endowing libraries to document their terms in office) was absolutely fascinating. 

We (re)discovered so much American history from the Great Depression through WWII packed into a small museum. We even got to see FDRs oval office desk and his personal study.
FDR's Personal Study

11. Enjoy an Art Deco Lunch at Eveready Diner

Get ready for an Art Deco fabulous lunch at Eveready Diner in Hyde Park, NY, just a 2 minute drive from the FDR Library and Home of Franklin D. Roosevelt National Historic Site. The Eveready Diner simply gleams in the sun on the outside thanks to the shiny chrome exterior and neon signs. 

The Eveready was featured on Diners, Drive-ins, and Dives with Guy Fieri and has gotten a lot of hype.
We found the menu to be rather overwhelming with all the choices. 

We settled on a diner classic pot roast and mashed potatoes plus broiled sole. A Vanilla diet coke washed it all down and we saved room for a slice of lemon meringue pie for dessert. 

So much food! Beware the giant American portions!
Things to do around Poughkeepsie, NY: Inside the Eveready DinerThings to do around Poughkeepsie, NY: Outside the Eveready Diner

SIDEWALK SAFARI SPOTLIGHT: Looking for more Art Deco travel inspiration in the United States? Why not spend a day exploring South Beach in Miami, Florida or the gorgeous Art Deco skyscrapers in San Francisco.

12. Make a Pitstop at Mills Mansion

Onwards to Mills Mansion with a brief stop to admire idyllic Staatsburg. The tiny village of Staatsburg NY had a surprising number of amazing doors. 

Take a quick drive around Mills Mansion. The stately home was originally built in 1832 but greatly expanded around the turn of the 20th century. 

More formally known as the mansion at Staatsburgh State Historic Site, Mills Mansion is posh example of the kind of home built by the ultra-rich industrial leaders during the Gilded Age.
Poughkeepsie Attractions: Mills MansionPurple door in Staatburg, NY near Poughkeepsie

13. Shop Rhinebeck 

The Hudson River Valley is dotted with quaint towns. We picked up coffee and some sour gummy pumpkins at Samuel's Sweet Shop in Rhinebeck, NY and then took a stroll around town. 

Very picturesque! Rhinebeck stood out to me largely due to its solid door game. I absolutely loved the Victorian ambiance.
Things to do near Poughkeepsie: Samuel's Sweet Shop in RhinebeckDoor with Victorian ambiance in Rhinebeck NY

14. Admire Saugerties Architecture

Saugerties, NY is another town worth stopping in on a day out from Poughkeepsie. The combination of amazing fall colors and architecture really caught my attention. Grab a sweet treat at the Hudson Valley Dessert Company before continuing your drive.
Things to do near Poughkeepsie: Saugerties New York architectureThings to do in the Hudson River Valley: Peace sign on a door in Woodstock, NY

15. Unleash Your Inner Hippie in Woodstock

Woodstock is possibly the most well-recognized town in the Hudson River Valley with notoriety arising from the Woodstock Music Festival held in the area in 1969. Today, Woodstock still enjoys a healthy hippie vibe (although you get the sense they are catering to tourists in this regard). 

We enjoyed browsing the cute shops in Woodstock which are a good place to pick up a souvenir in the Hudson Valley. 

Poughkeepsie Day Trips: South to Sleepy Hollow

We headed south on a Saturday to explore things to do around Poughkeepsie including some of the military and literary history of the area.  

16. Check out the West Point Museum

We started our day at the West Point Museum. Warning: Google Maps directs you to a place that is a restricted military installation. 

We got questioned sternly as we tried to turn around. Look for the tank by the side of the road which marks the entrance to the visitors center/museum.
Things to do around Poughkeepsie: West Point Museum

West Point Museum features exhibits about the history of the school, American wars, and warfare more broadly. Allow a couple hours to explore the free museum. There are four floors in all.

17. Seeking the Facts of Life in Peekskill

We thought it would be fun to visit Peekskill, the setting for the 1980s sitcom The Facts of Life. Instead of a walk down memory lane with Mrs. Garrett, Blair, Jo, Tootie, and Nathalie, we discovered a downtown historic district that has seen better days. 
Photowalk in Peekskill, NYElks Lodge in Peekskill NYParamount Theatre in Peekskill NY
We did see some cool architecture including a revived Paramount Theatre and Elks Lodge. We picked up a maple glazed pumpkin scone from the Cardamom Man at the Peekskill Farmers Market before continuing our drive south.

18. Experience the Legend of Sleepy Hollow

Onward to Sleepy Hollow! Parking was a little tricky. We went down to the river and ate al fresco at Hudson Farmer and the Fish Restaurant. We enjoyed Clam Chowder and polenta fries for a lunch snack. The views were better than the food.
Hudson River Views in Sleepy Hollow NY
We visited Washington Irving's grave at Sleepy Hollow Cemetery. We also took a stroll and found Andrew Carnegie's grave too. Near the Old Dutch Reformed Church, we spotted American flags marking the graves of those who fought in the Revolutionary War. 

A Headless Horseman statue stands just outside Sleepy Hollow Cemetery in a further nod to Irving's famous book The Legend of Sleepy Hollow.
Headless Horseman Statue in Sleepy Hollow

Grave stones at Sleepy Hollow Cemetery in the FallGrave stones at Sleepy Hollow Cemetery


I love visiting historic cemeteries. Mount Auburn Cemetery in Cambridge, Massachusetts is definitely worth exploring.

 Get a coffee around Bakery Square in Pittsburgh and then head to Homewood Cemetery where members of the Frick, Mellon, and Heinz families are buried.

19. Go For a Photowalk in Cold Spring

Things to do around Poughkeepsie: Antiquing in Cold Spring NY
We made one final stop on our southerly day trip from Poughkeepsie in Cold Spring. Cold Spring is a quaint town but a bit too crowded for my liking on a Saturday afternoon. 

We took a brief photowalk after we got lucky and found a parking spot on a side street. The doors of Cold Spring were simply the highlight for me. 

If I had to do it again, I'd visit Cold Spring for a coffee in the morning on a workcation day rather than on the weekend to avoid the crowds. You'll enjoy Cold Spring if you are into antiquing or photography. The antique shopfronts are simply stunning.
Door with a wreath in Cold Spring New YorkDoor with a white picket fence in Cold Spring NYOrange door on a blue house in Cold Spring NY

Summing up our Workcation in Poughkeepsie

As you can see, Poughkeepsie is an ideal home base for an Autumn workcation. The Fall foliage is spectacular. 

You'll find quaint towns to visit for a coffee before you start work and there is plenty to do in the Hudson River Valley both north and south of Poughkeepsie to easily keep you busy for a few action-packed day trips by car. 

SIDEWALK SAFARI SPOTLIGHT: Looking for more inspiration of things to do in and around New York City? Why not take a workcation in New York and explore coffee shops along the High Line or spend one day getting to know Brooklyn, NY.

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Things to do near Poughkeepsie, NYFall in the Hudson River Valley NY

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Sidewalk Safari | Part-time Travel Blog: 19 Fun Things to do around Poughkeepsie on a One Week Workcation
19 Fun Things to do around Poughkeepsie on a One Week Workcation
Looking for things to do in Poughkeepsie? Discover things to do around Poughkeepsie. Find the best attractions near Poughkeepsie NY on a workcation.
Sidewalk Safari | Part-time Travel Blog