Here Are Your Labor Day Weekend Plans

Meet a clan of award-winning alpacas, or groove to island jams in Peekskill.


Feeling a little bummed because you still haven’t made fun plans for Labor Day weekend? Don’t fret just yet. Break out your white pants for one final jaunt this summer at any of these local Hudson Valley gatherings.


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Pick-Your-Own at Barton Orchards 

This family farm is currently picking peaches, produce, and early-season apples, and this Saturday through Labor Day will also be hosting live music. Stop by the bakery for some of their award-winning fresh apple cider doughnuts or the taproom for a cool brew.

63 Apple Tree Ln, Poughquag


Food Truck Picnic Day at Olana 

Saturday, September 2, Frederic Church’s Olana estate will host the Gracie’s Luncheonette Food Truck from 11 a.m. to 7 p.m. so guests can enjoy delicious al fresco meals on the historic grounds. Bring your own chairs, blankets, coolers, and maybe set up an easel to paint your own renditions of the scenic landscape.

5720 State Route 9G, Hudson

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Photo by Anthony Bartley

Time Travelers Weekend at the New York Renaissance Faire 

No summer would be complete without a trip to this Tuxedo Park mainstay. For Labor Day Weekend, the Faire lets anachronism run wild: Fantasy Saturday encourages guests to “transform yourself into the mystical being of your dreams,” be it ice dragon, courtly fae, or majestic hippogryph. Steampunk Sunday lets visitors play up their love for alt-Victorian fashion sensibilities and clockwork filigree, or even the sleek tech of a far-flung future. Holiday revelers might also enjoy Barbarian Monday, during which a horde of invading barbarians with overrun the grounds and hold their Games of Strength and Endurance. Costume contests, parades, and themed games will run all weekend.

Tuxedo Park


Fall Harvest Festival Kick-Off at Wright Family Farm 

“The Wright place for farm fun” opens its gates for the fall season on Saturday, ushering guests into its pumpkin patch, petting zoo, corn maze, rides and more. As an added bonus, Labor Day weekend and the weekend following include a special offer of free entry with valid I.D. for U.S. military members and first responders, as well as their families.

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329 Kings Highway, Warwick


All-You-Can-Eat Pig Roast at Orange County Distillery 

Saturday, from 2 p.m. to 10 p.m., Hudson Valley’s own Orange County Distillery is teaming up with Boss Hog BBQ to host an all-you-can-eat pig roast at Brown Barn Farms. Beer and cocktails will also be available, as well as regular menu items from resident food truck “The Bus” (plus s’mores!), while live music plays all day. Tickets are $25 for adults, $9 for kids.

286 Maple Ave., New Hampton

Franz Josef Heinrichs | Flickr

Woodstock-New Paltz Art & Crafts Fair 

Only held twice a year, Memorial Day and Labor Day Weekends, at the Ulster County fairgrounds, represent a curated collection of round 300 local artists and craftspeople. Entertainment includes live music, craft demos and exhibits, animal shows, and more. Making a special appearance this Saturday through Monday are several award-winning alpacas from Kellogg’s Alpacas of Scio, NY!

249 Libertyville Rd, New Paltz


The West Point Band’s Labor Day Celebration 

The culmination of the West Point Band’s bicentennial season, Music Under the Stars will conclude with performances at Trophy Point by the West Point Concert Band, Hellcats, and Benny Havens Band, ultimately swelling to a rendition of Tchaikovsky’s 1812 Overture with fireworks display and live canon fire. Admission is free, so show up early for the 7:30 p.m. concert to lay claim to a good patch of grass (but not too early; the military police will clear the lot at noon to make space, and no one wants you to accidentally donate your lawn chairs). As always, drinks are BYOB and leashed pets are welcome, however do consider your pet’s reaction to loud noises (i.e., canons).

685 Hardee Place, West Point


BeanRunner Cafe Caribbean Labor Day Jam

The BeanRunner Café in Peekskill features live music every Friday and Saturday nights, which for Labor Day is means Salsa Night Friday with Ran Kan Kan (musician and radio host Chico Alvarez and flutist Mauricio Smith, Jr.) and Reggae Saturday featuring The Anthem Band. Each night runs 8 p.m. to 10:30 p.m., and admission is $15.

201 South Division St., Peekskill

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