The Best Way to Spend a Day in Poughkeepsie

From waffles to walkways, this daylong guide to Poughkeepsie, NY highlights the culture and history of the community.



WIKIMEDIA COMMONS/JULIANCOLTON

 

As the last stop on the Metro-North line from New York City, Poughkeepsie is an easy retreat for weekend warriors who crave riverside views in spring and foliage tours in fall. No matter what time of year, the waterfront city has it all. To make the most of a full day trip, intersperse local flavors with regional history and low key recreation. By the time nightfall rolls around, you may never want to leave.

 

 

8 a.m. – Order Instagram-worthy waffles at The Poughkeepsie Grind

Don’t go to The Poughkeepsie Grind for a cup of joe. Don’t just dash in and out for your daily dose of caffeine; do yourself a favor and order up one of the shop’s signature waffles to go along with the perfectly roasted Illuminated Coffee Co. java. The flavors change regularly, and have included decadent options like brownie and red velvet in the past. Whatever you order, expect the waffle to be bigger than your face and loaded with toppings galore.

107 Main St, Poughkeepsie
845.345.9588

Mon-Fri 6 a.m. – 4 p.m., Sat 8 a.m. – 4 p.m.

 

 

9:30 a.m. – Stroll along the Walkway Over the Hudson

If you can’t find a roadside spot, park the car in the Poughkeepsie entrance lot on Parker Avenue before beginning the trip across the Walkway Over the Hudson. The former railroad bridge is now one of Poughkeepsie’s top attractions, and for good reason. At the center point between Poughkeepsie and Highland, walkers get an unparalleled view of the Hudson River. Speaking of the middle ground, it may be where you choose to turn around and head back to the car. The complete loop to the Highland side and back is just shy of three miles.

Poughkeepsie Entrance  – 61 Parker Ave, Poughkeepsie
Elevator Entrance
 – 83 N. Water St, Poughkeepsie
Open daily 7 a.m. – sunset

 

 

mozzarella, prosciutto, tomato, basil and olive paste on fresh focaccia ☺️

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12 p.m. – Taste the flavors of Little Italy at Rossi’s

Housed in the heart of Poughkeepsie’s Little Italy neighborhood, Rosticceria Rossi & Sons is a holy grail for locals and college students alike. One step into the corner deli and you’ll understand why. Snatches of Italian fly through the air as the Rossi family slices fresh bread and roasted meat faster than seems humanly possible. Mix and match ingredients to form your own panino or order one of the hot dishes of the day. There is no space to chow down inside, so claim a table or head back to the river to picnic by the water.

45 South Clover St, Poughkeepsie
845.471.0654

Mon-Fri 7:30 a.m. – 6 p.m., Sat 8 a.m. – 5 p.m.

 

 
 
 
 
 
 
 
 
 
 
 
 
 

Locust Grove Estate 🏡 a National historic landmark the home of Samuel F B Morse circa 1851

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1:30 p.m. – Explore local history at Locust Grove

Put down the phone and try the telegraph at Locust Grove Estate. The former home of Morse code inventor Samuel Morse is now a public estate that spans 200 acres in Poughkeepsie. Although the sprawling grounds are ideal for walks or hikes, take time to head indoors to explore the mansion that Morse commissioned in 1850. Throughout the year, the visitor center houses local artist exhibitions as well.

2683 South Rd, Poughkeepsie
845.454.4500

Apr – Dec, open daily 10 a.m. – 5 p.m. Jan – March, Mon-Fri 10 a.m. – 5 p.m.

 

 

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3 p.m. – Channel your inner artist at the Poughkeepsie Underwear Factory

As the name suggests, the brick building tucked away on North Cherry Street used to be a site for underwear production. Nowadays, however, the renovated space is a thriving community hub. The first floor is dedicated to food, thanks to the open kitchen space, coffee house, and lunchtime eatery. The second floor is where the art happens. Newbies and experienced artists alike can enroll in a printmaking class or stop in for studio hours during the week. Whether you watch the process or print your very own t-shirt, you’ll be hooked on crafting in no time.

8 North Cherry St, Poughkeepsie
845.337.0263

Mon-Fri 8 a.m. – 4 p.m.

 

 

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5:30 p.m. – Travel around the world for dinner at Twisted Soul

Twisted Soul is one of Poughkeepsie’s hidden gems. Located a hop, skip, and a jump away from Vassar College, the pint-sized kitchen blends flavors from every corner of the world to create dishes that need to be eaten to be truly appreciated. The menu changes regularly, so come back often. Fortunately, the goat cheese empanadas and pulled pork mac and cheese are beloved staples. For dessert, treat yourself to a signature cupcake, preferably one that oozes dulce de leche cream from the center.

47 Raymond Ave, Poughkeepsie
845.454.2770

Mon, Wed, Thurs 11 a.m. – 8 p.m., Fri 11 a.m. – 8:30 p.m., Sat 12 p.m. – 8:30 p.m.

 

 

#openmic tonight! Sign up at 6:30, show starts at 7!

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7 p.m. - Sign up for an open mic night at The Crafted Kup

Feeling brave? Show your stuff at The Crafted Kup’s CK Open Mic sessions. Tune into the shop’s Facebook page for news about the next session. Even if you decide not to venture in front of the microphone, grab yourself a chair, and take in the best of what the local talent has to offer. If you need a jolt of caffeine to keep jamming to the tunes, java is ready on tap.

44 Raymond Ave, Poughkeepsie
845.483.7070

Mon-Wed, Fri 7 a.m. – 7 p.m., Thurs 7 a.m. – 9 p.m., Sat-Sun 8 a.m. – 6 p.m.

 

 

8:30 p.m. - Rest your eyes at the Poughkeepsie Grand Hotel

After you belt out a few verses at open mic night, rest your vocal cords – and your eyes – at the Poughkeepsie Grand Hotel. Conveniently located near the Poughkeepsie train station, the hotel is a classic, locally owned space with all the amenities you crave of an overnight. Dive into a bed in a double or king room in the evening, then wake up refreshed the next day to dig into a complimentary American-style breakfast. If you’re planning to jaunt south to NYC on Metro-North or north to Albany on Amtrak after a weekend in town, the Grand is the way to go.

40 Civic Center Plaza, Poughkeepsie
845.485.5300

Did we miss a spot? Let us know where to go to find the best of Poughkeepsie in the comments or by email at edit@hvmag.com.


Related: How to Spend a Saturday in Hudson

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