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

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Cocktails at Iron Vine. Photos by Doug Schneider

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. – Coffee and a Light Breakfast at The Central

One of Peekskill’s newest additions, this cozy café inside the old Peekskill Train Station Ticket Booth 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 will soon also open as a full-service bar and restaurant in the evenings, making it the perfect place to hit up happy hour on your train ride home.

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.

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“Gold Capped Diver” stature at Riverfront Green Park

12 p.m. – Go for brunch

Choose between two of the city’s most popular Saturday brunch options. Fin & Brew (5 John Walsh Blvd; 914.788.4555) offers classic mid-morning fare and an eggs Benedict that will knock your socks off, along with a well-stocked raw bar. Or make your way up to Main Street for a beer-laden brunch of elevated pub food at Birdsall House (970 Main St; 914.930.1880).

1 p.m. – Explore 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. The intimate space is currently celebrating its 25th anniversary with discounts and specials on 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.

1:30 p.m. – Shop ’til you drop

Along the way, drop some cash along the city’s main shopping street. Browse five 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 furnishings and boho chic fashion at Bucko! (107 S Division St; 914.214.9143).

peekskill - bruised apple

The selection at Bruised Apple Books is quite cozy — and extensive.

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 (about 50,000 titles!) of rare books and vinyl.

3:15 p.m. – Get your coffee fix

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).

4:00 p.m. – Brush up on contemporary art

You’ve got about two hours 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.

6:00 p.m. – Grab a drink

It’s time to check out the bar scene. At Iron Vine (992 Main St; 914.930.8507), reclaimed décor from historic Peekskill sets a speakeasy vibe for expertly executed cocktails. 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 River Outpost Brewing Co. (5 John Walsh Blvd; 914.788.4555).

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.

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 surf and turf, and the eponymous soft shells at Taco Dive Bar (55 Hudson Ave; 914.788.8226) are all excellent choices.

9:30 p.m. – Hit the town

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


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

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