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How to Spend a Saturday in Peekskill

Cocktails at Iron Vine
Photos by Doug Schneider

Dive into the hip and bustling city with a full day of outdoor adventures, boutique shopping, artistic endeavors, and extravagent eats.

What is it about Peekskill that makes it so cool? In recent years, our county’s northernmost city has adopted an almost Harlem-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.

10:30 a.m.

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 at www.hvcca.org). After you’ve found them all, explore Riverfront Green Park and walk a stretch of the newly expanded RiverWalk.


Choose between two of the city’s most popular Saturday brunch options. Tender tacos at Taco Dive Bar (55 Hudson Ave; 914.788.8226) feature tortillas from nixtamal La Milpa de Rosa in Yonkers. (Hudson Creamery serves ice cream sundaes next door in warmer weather.) 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.

Seek out Gallery 982 (982 Main St; 914.930.8280), hidden on the second floor. The intimate space’s current exhibit features a mix of established artists and new talent whose pieces have never been galleried before. Depending on the season, you can also try one of the many local galleries that dot the very walkable Main St-South Division area all the way up to the Paramount and Peekskill Coffee House at the historic Flat Iron Building.

1:30 p.m.

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 antique items from Flat Iron Gallery (105 S Division St; 914.734.1894).

2:45 p.m.

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.

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 a warm Belgium waffle, too). If tea is more your speed, Kathleen’s Tea Room (979 Main St; 914.734.2520) serves more than 50 varieties with a side of classic charm.

4:00 p.m.

You’ve got about two hours to explore one of the county’s preeminent museums. The Hudson Valley Center for Contemporary Art (1701 Main St; 914.788.0100) displays 12,000 sq ft of curated exhibits.

6:00 p.m.

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. If you’re willing to drive a few minutes, a tasting flight in the Tap Room at Peekskill Brewery (47 S Water St; 914.734.2337) is a must for local beer enthusiasts.

8:00 p.m.

For dinner, dip chopsticks into a bowl of brothy noodles at RameNesque (1008 Main St; 914.930.1788), 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.

9:30 p.m.

Make your way to The Hudson Room (23 S Division St; 914.788.3663), where it’s standing-room-only for live music starting at 10 p.m. on Friday and Saturday nights.

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