Peekskill is the best small city within 50 miles of Manhattan. Debate me all you want. I’ll never be swayed. I have lived here for about ten years. I’ve seen this place go from a struggling underdog of a city to all it is now.
I talk about Peekskill constantly but honestly it’s one of those places that makes me happier than anywhere in the world.
While prepping for a visit from a friend to see my hometown, I pulled together all we need to see and do and thought it’s worth sharing since I can’t be everyone’s tour guide (as much as I’d love to be).
1) Hang out down by the train station- If you’re coming by train you’re going to arrive here anyway. Take a stroll along the River Walk and see some beautiful art along the way set perfectly with the backdrop of the Hudson River. After your walk, grab a beer at Peekskill Brewery. Eat lunch there or hit Taco Dive Bar or Bourbon and Buns. Save room for dessert with ice cream at Hudson Creamery or a pastry from Homestyle Bakery. Impress a friend by grabbing some wine at Dylan’s Wine Cellar and chat with Steve about which vintage to choose (cause Steve is awesome).
2) Go on a Coffee Shop Crawl- Downtown Peekskill has three awesome coffee shops all within walking distance of one another. Have avocado toast or a vegan treat at Kurzhal’s. Catch a jazz session or grab a sandwich at The Bean Runner. Enjoy crepes and conversations at Peekskill Coffee House (and see me write there every weekend, though, that’s not much fun to watch). Honorable mention to Baisley’s Deli, (which is not downtown but on Hudson Ave) and has the ice coffee served in cups they keep in the ice cream freezer. Also, they do not judge me when I go back to get a second or third cup in a single day.
3) Brunch it Up- Endless Mimosas along with delicious egg dishes are available in the jewel box space that is Iron Vine. (Try the “Cool and Proper” since it’s been named the best cocktail in Peekskill by me.) Is it gorgeous out? Then eat outdoors at Birdsall House and try their French toast or pancakes. Want a spot of tea and one of the best scones you’ll ever have? Hit up Kathleen’s Tea Room, but make a reservation first.
4) Support Some Unique Small Businesses– Jeorgia at the Quirk Shop upcycles cashmere into gorgeous hats and sweaters. Find that perfect little gift for someone special at The Coop. Treat yourself to a massage at Jo’s Body Shop, where you’ll walk out feeling amazing or join a yoga class at Family Dog Yoga (where Brigid, my favorite instructor will help you Namaste). Grab a fresh juice at PK Blendz. Buy an old vinyl and a book at The Bruised Apple. Read a comic book at The Rift. Indulge your inner rock star at Division Street Guitars. Get amazing body art at Speakeasy Tattoo Studio. (I’m fairly certain 50% of Peekskillians have ink from this place.) And admire the gorgeous light displays on The Division Street Grill and at the Evening Star created by
Vivid RGB Lighting
5) Get cultured- Go to a show at the Paramount. Wander the galleries downtown or see the latest exhibit at Hudson Valley Center for Contemporary Art. Live music is everywhere!!! Catch Peekskill’s own Phineas and the Lonely Leaves at River Outpost Brewery where their epic set honoring Tom Petty is a thing of legend! Drag Night happens monthly at Birdsall, brought to you by the amazing Dolly Spartan. Or try Let’s Go Trivia every Wednesday (and eat the best pizza) at Gleason’s.
6) Got a Kid or wanna be one for a day: Sweet Ascent where you can get a history of candy. Hit up Spins Hudson where you can play video games, challenge your friends to laser tag and even do a ropes course. The Peekskill library has an adorable section for children’s books with tons of things to do with your little one.
7) Travel the World downtown- Start with some Korean influenced cuisine at RameNesque (their outside garden in back in a secret treat). Have a pint in England at McDonald & Peacock Cider House and then Ireland at The Quiet Man. Ruben’s has killer Margaritas. The Eagle Saloon takes you on a domestic flight to Nashville where you can do a shot of whiskey while you listen to country music. And The Hudson Room has the best sushi in town. (I still need to try A Touch of Class that serves Caribbean Fusion Cuisine.)
I am probably forgetting so many things but you really have to come to fully get it. The people are what truly makes Peekskill. I’ve never lived anywhere that felt more like a community. It’s a place where everyone can disagree on a million things, but we can all agree to love being here.
What are you waiting for? Come see if Peekskill is perfect for you.