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Peekskill Labor Day Weekend Guide: Top Things to Do

Labor Day Weekend marks the beginning of the end of summer in the Hudson Valley, and it’s a chance to squeeze as much out of these long warm days as possible before the cool breezes of autumn start. We’ve created this handy guide to help you make the most of this long weekend in Peekskill and beyond.

1. Cruise the Hudson River on NY BOAT CO. (and save 15% with our promo code!)

The Evening Star in Peekskill Bay

Peekskill’s very own NY BOAT CO. sets sail from the Peekskill Riverfront Green Park through October, but this weekend could be one of your few remaining chances to ride the Evening Star without needing to bundle up. NY BOAT CO. will offer Sunset Cruises, River Trips, and One Hour Boat Rides (perfect for traveling with small children) for the entire long weekend. If you use our promo code EXURB15 at checkout you’ll save 15%! Head over to the NY BOAT CO. website to book now!

2. Cool down at Peekskill’s public pool in Depew Park

The Peekskill Veterans Memorial Pool in Depew Park on an overcast day.

Veteran’s Memorial Pool in Depew Park is Peekskill’s public pool and it’s a fabulous summer destination for residents looking to beat the heat — so fabulous that we wrote a guide to using it! The pool closes for the season after September 4th (Labor Day) so this is your last chance to take advantage of it this summer.

3. Take a farm tour at Hemlock Hill Farm

Sheep grazing at Hemlock Hill Farm.

September marks the start of weekly farm tours at Hemlock Hill Farm in nearby Cortlandt. Tours start at 10:30am and 12pm. They are 45 minute walking tours. The farm tours share the family history, techniques and practices and explain how the farm works as a whole. $5 per person, kids 2 and under are FREE! And don’t forget to stop at their farm market for some of the freshest local meat you can get for a Labor Day BBQ.

4. Soak up the sun at the Peekskill Riverfront Green Park

Live music and crowd on the lawn at Peekskill Riverfront Green Park.

The Riverfront Green Park is arguably Peekskill’s greatest asset, and the summer is when it really shines as residents and visitors gather along the shore of the Hudson to take in the breathtaking river and mountain views that stretch almost of entire length of the city limits. There’s a great playground for kids, a sculpture trail, pavilions to grill that meat you bought from Hemlock Hill Farm, a kayak launch at Peekskill Landing, and a riverwalk that leads to our next suggestion located at the south end of the riverfront…

5. Have an end of summer blast at Factoria Charles Point

The sunsets over the picnic table dining area at River Outpost Brewing Co. in Peekskill, NY

Factoria at Charles Point is Peekskill’s premiere entertainment and dining destination located right on the Hudson River and it’s really its best during the summer where the ample outdoor space can be fully enjoyed. If you’re lucky enough to have a boat, you can dock for free at Charles Point Marina for dock and dine and River Outpost or Fin & Brew. Bring the kids to Spins Hudson for arcade games, laser tag, and a ropes course. River Outpost will have live music all weekend: DJ Vinnie Campisi on Friday, HERE24 on Saturday, and Chris Raabe on Sunday.

And on Sunday from 4pm – 10pm Factoria will be hosting the FREE Hudson River Music & Comedy Fest!

6. Bring the kids to the Spray Pool at Lepore Park

Lepoe Park Spray Pool in the summer

One of Peekskill’s centrally located urban parks — Lepore Park on Main Street — contains within it a hidden gem: a spray pool (we prefer to call it a splash park) perfect for little ones to safely cool off. The water features invite children to splash, run, and play. The spray pool season ends on September 6, so this is your last weekend to take advantage of it this summer.

7. Take a forest bath in Croton

Forest Bath Walks

Forest Baths is a Peekskill based “forest therapy guide” offering immersive forest therapy experiences throughout the Lower Hudson Valley. On Sunday from 4pm – 6pm they will be offering a guide forest bathing walk from Croton-on-Hudson. Tickets cost $30 and can be purchased on the Forest Baths website.

8. Snag a sandwich at Benny’s Brown Bag

A crew of people in front of Benny's Brown Bag in Peekskill

Peekskill’s coolest deli opened this summer and it’s located right across from Peekskill High School, so do yourself a favor and head to Benny’s Brown Bag this weekend to grab one of their many amazing specialty sandwiches before the back-to-school rush. You can’t go wrong with anything on the menu, but we’re partial to the Chimi Chimi Ya Roast Beef. Oh, and they have a fully stocked fridge of curated craft beers for your Labor Day BBQ.

9. Shop the end-of-summer sale at Lounge House

Ladies, this weekend The Lounge House is clearing out their summer stock and it’s your chance to save on their cute collections. All summer items including dresses, accessories, hats, and tanks are just $15! On Saturday and Sunday, they’ll have bubbly while you shop and if you spend $150+ you can get a free permanent bracelet.

10. Vist our Peekskill Events Calendar to make sure you don’t miss a thing this Labor Day Weekend

In addition to our suggestions here, our Peekskill Events Calendar is chock full of great music, market, foodie, and cultural events happening in and around Peekskill this weekend. Round out your to-do list with a visit, and bookmark it because we’re constantly adding new events!