What You May Not Know About Peekskill

By Kaitlyn Hardy

Photography by Justin Negard and Vincent Negard

Once a stop along the Underground Railroad and now a burgeoning hub of art and culture, the streets of Peekskill are dotted with history.

Jo-Ann Brody, the former owner of an art gallery in the town who is now the communications and gallery coordinator at the Hudson Valley Museum of Contemporary Art, remembers the days when Peekskill needed a little love. Brody says the city had “the perception that there was a lot of crime. It wasn’t safe; it was not nice.”

In the early 1990s, however, an initiative by city planner Ralph DiBart brought a migration of artists to Riverside City. This project turned vacant spaces into artist housing and opened galleries throughout the city, helping it grow into the lively community it is today.

In the wake of his plan’s success, “the downtown suddenly had people living in it that were going out, were interested in the schools, interested in keeping it clean,” Brody recalls.

Alongside the galleries lie relics of history, including several safe houses that were part of the Underground Railroad.

The city is in the process of installing a series of murals honoring this history, an effort that is just one part of a $10 million Downtown Revitalization Initiative (DRI), courtesy of a grant gifted to the city in February 2024. One of the murals, a portrait of abolitionist Harriet Tubman, watches over South Division Street, right above The Fern Tree, a clothing and gift store owned by Lafern Joseph, a Peekskill resident since 1989.

“They’re gorgeous, they’re colorful, they’re representative of the community,” Joseph describes. “It’s a gift.”

There is so much to celebrate in Peekskill that it can almost be overwhelming. So if you haven’t been to Peekskill in a while, here’s what you may not know.

The Hudson Valley Museum of Contemporary Art.

Things to do

Since the 1990s, Peekskill has been largely known for one thing: art. There are galleries, street art, art studios, art alliance groups, art events and more. The Hudson Valley Museum of Contemporary Art (MOCA), which has become somewhat of an art mecca in Westchester, is currently showing its fifth juried art show, “So you think you’re too old to…”—it’s an exhibition comprised of artists 62 years and older, the oldest artist being 92 years old.

“It’s based on the idea that artists, at a certain point, become more of who they are,” Brody explains. “My mother always said, ‘You don’t change; you become more of who you are.’ So we got a lot of quirky submissions, as [the artists] said, ‘I don’t care if you judge me anymore; this is who I am!’”

Harriet Tubman mural overlooking South Division Street, above The Fern Tree.

With 72 pieces by 68 artists, you’ll find a variety of extraordinary, innovative and even “quirky” pieces, including Carol Bouyoucos’ brightly colored floral post-photographic mural “Still Life in the Wind” that “re-imagines the narrative of nature’s rapid reshaping,” Sydney Cash’s “ADHD Party” featuring numerous brightly colored snippets of abstract art set behind rippled glass, giving you the illusion of movement as you walk by and Timothy Lutz’s “Stella Maris” wood and canvas sculpture of a woman in the shower.

And, of course, there are several other galleries you can check out, including Flat Iron Gallery and Third Eye Arts. Or, simply stop into a coffee shop, such as Peekskill Coffee House or Bean Runner Cafe, where local artists’ works are hung on display.

“Our artists change every month,” says Sunny Cover, owner of Peekskill Coffee House. “We usually have over a year-long waiting list for artists.”

With such a large art environment, singer and visual artist Bria Waterman (a.k.a. Bria the Artist) says it can be hard to find a niche, but Peekskill artists are supportive of each other. Organizations, such as the Peekskill Arts Alliance and the Peekskill Arts Council—of which Waterman is a member—promote events and collaborations with businesses and other artists, keeping the city’s artistic vibrancy alive.

Vintage shop.

Or if you’d like to make art yourself, businesses such as RetakeRemake and Quirkshop offer crafting workshops, teaching everything from crocheting and knitting to calligraphy and songwriting. Both shops strive to reduce waste in the arts and crafts world by using donated and upcycled materials, weaving a chain of creation from donor to artist.

In the evenings, the Paramount Hudson Valley Theater hosts concerts, comedy shows and talks; their upcoming shows include Kathy Griffin (March 28), Fran Lebowitz (May 9) and Don McLean (May 31). The building has been a touchstone for entertainment since the 1930s, when it was built as a movie theater for Publix Pictures, a subsidiary of Paramount Pictures. By the late 1970s, the theater’s popularity waned, though its role as a Westchester County landmark has kept it standing. In 2006, a $1 million grant from NY State helped restore the classic theater to its former beauty, and in 2013, the theater became a not-for-profit arts organization.

Another way to step into Peekskill’s past is to take an Underground Railroad Tour. The tour, hosted by Joseph, stops along historic sites such as the African Methodist Episcopal Zion Church and the house at 112 Maine Street, both of which served as safe houses. You’ll also tour the home of abolitionists Harriet and Hawley Green and “the only documented surviving [Underground Railroad] tunnel in the country,” according to the Underground Railroad Tours’ brochure.

In warmer months, Peekskill’s riverfront offers a myriad of activities, from picnicking and kayaking to simply strolling along the river or watching the sunset glisten on the Hudson. As part of the 2024 DRI grant, nearly 20 sculptures were installed along the waterfront, adding an additional view to the existing one.

“I think [Peekskill] is a great place to come up for the day just to get a little bit of nature,” says Cover.

Outside El Sueño, Latin Lounge & Kitchen.

Where to eat

In Peekskill, dinner usually comes with a show. Restaurants such as Bean Runner Cafe (known for their calendar of jazz performances), Gleason’s and the River Outpost Brewery all host local musicians, holding intimate concerts in their dining rooms or backyards.

Right along the Hudson River lies River Outpost Brewery, a jack-of-all-trades for food and entertainment; it presents a hefty menu of traditional fare and beers brewed on location. In addition to a steady lineup of local artists, the restaurant-slash-venue hosts weekly trivia nights on Thursdays.

There’s also trivia on Wednesday nights at Gleasons, or, if you’re brave, join them for Thursday night karaoke. For the non-attention seekers, we recommend you come for their signature pizzas, and, after a few drinks, you’ll happily offer your (amazing, we’re sure) rendition of “Piano Man” or “Sweet Caroline” or whatever your go-to karaoke song might be.

Later in the night, head to El Sueno, a cozy, recently opened cocktail lounge and restaurant. If the warm, pink-like glow from the restaurant’s storefront doesn’t draw you in, the intoxicating scent of espresso martinis and citrus will.

Paramount Hudson Valley Theater.

Shopping

Peekskill thrives on its businesses, says Frances Berry, a 95-year-old resident of Peekskill who has lived there her whole life.

To keep with the artistic spirit, shops such as The Bruised Apple, a cozy book-lined grotto with hand-written notes decorating the walls; Division Street Guitars, a one-stop shop for guitar shopping and repairs owned by Paul DeCourcey who is a musician himself; and Early Electrics, a lighting design studio and showroom displaying intricately crafted lamps and chandeliers, cater to the artists and art-loving folks of Westchester and beyond.

To shop for a new wardrobe, Quirkshop and Stark Vintage curate sustainable yet stylish selections. Stark Vintage specializes in 1970s-2000s-style streetwear, holding an impressive collection of vintage t-shirts. Quirkshop, meanwhile, gives in to the boho spirit of the arts, selling jewelry and clothing handmade with recycled materials by owner Jeorjia Shea and other independent artists.

Or, stop into The Fern Tree, owned by Joseph, which offers a tapestry of African art, clothing and gifts, as well as a redolence of incense scents. The shop hosts fashion shows, concerts and holiday celebrations, and it’s also one of the home bases of the community, with Peekskill residents stopping in just to say hello and share a conversation with Joseph.

“We have people who believe in community,” Joseph says, not just referencing her store but the town of Peekskill as well.

This article was published in the March/April 2025 edition of Connect to Northern Westchester.