Town Guide #19: Peekskill

Welcome to HUTS nineteenth Town Guide, explore Peekskill with us! This town is known as the gateway to the Hudson Highlands and looks over the bank to the Hudson river. With a bustling downtown Peekskill is just an hour outside of the city and makes for the perfect getaway.

Photo by Gleasons

Where to eat:

Farm to table pizzas are their specialty at Gleasons. Along with creative craft cocktails you’ll be giddy at Gleasons. With their clever names these HUTS recommendations will make for an unforgettable meal; try the Bitter Heart cocktail paired with “Figgettaboutit” pizza.

What to do outside:

Ride around town with Pedal Peekskill to feel the river breeze through your hair. Bike along the riverfront and stop around town to refuel or pop in some shops. Be sure to ask the staff for their favorite rides in the area if you want to branch out. In April through November you can ride over to the Farmers & Flea Market to find some real treasures rain or shine!

Photo by Hudson Valley MOCA

What to do inside:

If indoor activities are more your speed check out the highly esteemed Hudson Valley MOCA for some amazing exhibitions and events by local artists. The exhibits here are sure to spark conversation for your weekend getaway and may keep you thinking for months to come. 

Photo by Airbnb Superhost Suzette

Where to stay:

Stay in this charming 1920s craftsman home and have fresh eggs from the chicken coop in the yard! What more could you want for a weekend upstate? After all of your adventures around town you’ll cozy up with a good book and dream of your own life upstate. Click here to book this Airbnb.

Featured Land Listing: 

This 3.94 acre lot just outside of downtown Peekskill is the perfect spot to build your own Upstate getaway. At $59k this lot can leave room in your budget to make your dream home a reality. Click here for more details on the listing!