Peekskill Day Trip Guide: How to Spend 24 Hours in Town

We’ve got you covered if you find yourself in the county’s northernmost city.

Cocktails at Iron Vine. Photos by Doug Schneider unless otherwise noted

Dive into the hip and bustling city with a full day of outdoor adventures, boutique shopping, and extravagant eats in our guide to Peekskill.

What is it about Peekskill that makes it so cool? In recent years, our county’s northernmost city has adopted a very Brooklyn-like vibe, with carefully restored historic charm, a vibrant dining scene, public art installations and galleries, and eclectic shopping. Here’s how to experience it all.

9:30 a.m. – Savor coffee and a light breakfast at The Central

One of Peekskill’s coziest cafés is located inside the old Peekskill Train Station Ticket Booth. It serves up house-made pastries and a light menu of early morning eats done to perfection. Convenient for morning commuters as well as locals, The Central opens as a full-service bar and restaurant from 12-10 p.m., making it the perfect place to hit up happy hour on your train ride home.

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the central
Photo by Dave Zucker

10:30 a.m. – Explore the local art scene

Start your Saturday with fresh air and a fresh perspective on Peekskill’s art scene. A dozen public works of art are clustered around the Metro-North station (a sculpture map showing installations across the city can be found here). After you’ve found them all, explore Riverfront Green Park and walk a stretch of the expanded RiverWalk.

“Gold Capped Diver” stature at Riverfront Green Park

12 p.m. – Go for brunch

Choose between two of the city’s Saturday brunch spots. Birdsall House (970 Main St; 914.930.1880) offers a beer-laden brunch of elevated pub food. Or you can make your way to a classic mid-morning fare and a weekend brunch special loaded with eggs, your choice of pancakes or Belgian waffles and your choice of breakfast meat on the side at BeanRunner Cafe (201 S Division St; (914) 737-1701).


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1 p.m. – Wander though The Flat Iron Gallery

Seek out The Flat Iron Gallery (105 S. Division Street; 914.734.1894), hidden on the second floor of the city’s famed Flatiron Building. In the intimate space, you can purchase local paintings and photography, jewelry, pottery, textiles, and even hand-blown glass pieces. Depending on the season, you can also try one of the many local galleries that dot the very walkable downtown area.


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1:30 p.m. – Shop ’til you drop in Peekskill

Along the way, drop some cash along the city’s main shopping street. Browse decades of Gibson and Fender at Division Street Guitars (36 N Division St; 914.737.2630), try on an eclectic mix of artisan jewelry, accessories, and clothes at Quirkshop (23 N Division St; 201.835.5719), and give your home a little vintage flare with funky home décor and boho chic fashion at Bucko! (107 S Division St; 914.214.9143).


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2:45 p.m. – Browse the stacks at Bruised Apple Books

Backtrack slightly to hit Bruised Apple Books (923 Central Ave; 914.734.7000). A Peekskill institution since the ’90s, the shop is famous for its expansive selection of rare books and vinyl.

peekskill - bruised apple
The selection at Bruised Apple Books is quite cozy — and extensive.

3:15 p.m. – Get your coffee fix in Peekskill

Fight off that mid-afternoon slump with a quick caffeine fix. Settle into one of the comfy chairs at Peekskill Coffee House (101 S Division St; 914.739.1287) for a cup of organic coffee with an emphasis on sustainable practices (order some sweet and savory crepes, too).


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4 p.m. – Brush up on contemporary art

You’ve got about an hour to explore one of the county’s preeminent museums. The Hudson Valley Museum of Contemporary Art (1701 Main St; 914.788.0100) displays 12,000 square feet of curated exhibits.

6 p.m. – Grab a drink in Peekskill

It’s time to check out the bar scene. At Iron Vine (992 Main St; 914.930.8506), reclaimed décor from historic Peekskill sets a speakeasy vibe for expertly executed craft beverages. Nearby, Whiskey River (38 N Division St; 914.293.7550) offers up some truly killer burgers and pub food, along with a rotating menu of innovative creations. Alternately, head back towards the river for a tasting flight in the Tap Room at Peekskill Brewery (47 S Water St; 914.734.2337) or a night of Dave-and-Buster’s-esque food, libations, and arcade games (also: axe throwing!) at Spins Hudson, with onsite food and drinks provided by River Outpost Brewing Co. (5 John Walsh Blvd; 914.788.4555).

8:00 p.m. – Time to dine

For dinner, dip chopsticks into a bowl of brothy noodles at RameNesque (1008 Main St; 914.402.1957), where the ramen — and everything else — is free of MSG. Not in the mood for noodles? Gleason’s (911 South St; 914.402.1950), named for the famed comic, is popular for its thin-crust pizza, while Iron Vine‘s taps, Fin & Brew‘s raw bar, and the eponymous soft shells at Taco Dive Bar (55 Hudson Ave; 914.788.8226) are all excellent choices.

peekskill guide - ramenesque
Ramenesque is now a full bar and restaurant, serving not just the savory noodle soup, but also curry, potstickers, and fresh sushi.

9:30 p.m. – Hit the town in Peekskill

Make your way downtown for the nightlife, where live music is a commonality at Birdsall House, seasonally along Division St, and at upscale cocktail lounge The Pink Iguana (21 S Division St; 914.788.4663).


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Read More: Spend the Perfect Saturday Close to Home With Our Handy Day Trip Guides

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