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Cinco de Mayo celebration with the "Upstate Weekend Plans" text written across the photo for the Hudson Valley, NY.

What To Do In The Hudson Valley This Weekend May 5 – May 7

By inside + out | May 4, 2023

Celebrate Cinco De Mayo with Salsa Dancing, Tequila Tasting, a Bridal Boutique Show & more! The Hudson Valley has events for all ages this weekend 🥂 Take your pick below…

🌭 Catskill, Fri May 5th. First Fridays Catskill.
An ALL-Day celebration of the community with extended hours, sips & snacks, pop-ups, discounts, music, & FUN on the FIRST FRIDAY of every month! Info HERE.

🚘 Rhinebeck, Fri May 5th – Sun May 7th, 12:00 PM – 5:00 PM. Rhinebeck Car Show.
Friday is the Swap Meet. Saturday are Hot Rods Customs, Race Cars, Compact Customs and Pickups. Sunday is the Classics! Info HERE.

👩🏻‍🎨 Beacon, Fri May 5th, 5:00 PM – 6:00 PM. Fun 4 All: Happy Cinco De Mayo.
Vincent’s Eat-Paint-Love Studio invites you to bring your friends out to paint their own canvas! Info HERE.

🧰 Montgomery, Sat May 6th, 11:00 AM – 5:00 PM. MADE Market.
Peruse local makers and the bounty of the Hudson Valley held at City Winery! Info HERE.

💃 New Paltz, Fri May 5th – Sun May 7th. Latin American Celebration. 
Mohonk welcomes you to join in the fiesta & traditions; featuring Salsa & Cha-Cha dance instruction, Calaveras painting, a tequila tasting, as well as chip & salsa bars! Info HERE.

👰 Beacon, Fri May 5th – Sun May 7th. Bridal Trunk Show.
Lambs Hill Bridal Boutique will be show casing the latest dresses from top designer, Justin Alexander! Info HERE.

🐐 High Falls, Sat May 6th, 10:00 AM – 1:30 PM. Open Day First Tour of the Season.
Woodstock Farm Sanctuary opens their barn doors for the tour season! Info HERE.

🛠️ Woodstock, Sat May 6th, 10:00 AM – 2:00 PM. Woodstock Repair Cafe.
Come get your beloved but broken items fixed–for FREE!–by volunteer repair coaches who are also your neighbors. Info HERE.

♻️ Hudson, Sat May 6th, 12:00 PM – 3:00 PM. OLANA State Historic Site: I Love My Parks Day.
Free Landscape tour and Volunteer Day of Service to help clean up the public lands surround OLANA. Info HERE.

🍸 Fishkill, Sat May 6th, 12:00 PM – 4:00 PM. The Hudson Valley’s Ultimate Tequila & Mezcal Experience.
Head on out to 18 North Grill to try & explore the Agave space with Tequila, Mezcal, & check out Sotol! Info HERE.

🍎 Accord, Sat May 6th – Sun May 7th, 11:00 AM – 6:00 PM. Spring FINDINGS.
A garden-themed Vintage, Makers, and Farmers Market at Stone Ridge Orchard featuring 80+ curated regional vendors, beautiful antiques, and gorgeous handmade goods. Info HERE.

🤘🏽Woodstock, Sat May 6th + Sun May 7th, 10:00 AM – 11:00 PM. Woodstock Rock Art and Poster Show.
Over 40 exhibitors ranging from painters to printers, body artists to serious art collectors gathered to share their love for and knowledge of the art form known simply as “rock poster”. Info HERE.

⚾️ Wappingers Falls, Sun May 7th, 2:05 PM – 5:30 PM. HV Renegades Environmental Fundraiser.
Hudson Valley Renegades sponsors the Catskill Center for a  Fundraiser at their HV Renegades vs. Wilmington Blue Rocks baseball game. A home run for the environment! Info HERE.


👉 Know of more cool events happening in the Hudson Valley/Catskills area?
Leave them in the comments below.

Have a wonderful weekend from Inside+Out Upstate NY!


  • Grab your blanket and chairs and celebrate with us at our 12th anniversary of Putnam County Wine & Food Fest on the majestic view of Hudson Valley. The fest takes place Saturday, August 5, 11 am to 6 pm, and Sunday, August 6, 2023, 11 am to 5 pm, at Wells Park, 98 Oak Street, Brewster, NY 10509.

    This family fun-filled fest highlights the abundance of food and spirits available in the Hudson Valley and beyond. It provides an ideal day in the country for anyone who loves the farm to table and artisanal lifestyle. You can sip wine, spirits, cider, and, if you like what you have tasted, you can purchase it either in the bottle or the case. Listen to live music, while you shop from additional vendors including honey, olive oil, fine crafts, specialty foods, food vendors including the beer tent which are available to purchase during the event. It also features cooking and mixology demonstrations and various activities for everyone including the kiddies, which features face painting, rides, sand arts and other games.

    Food and beer are not included in the admission price. Tickets are Non-refundable. Rain or Shine. Children ages fifteen and under admitted free.

    Getting to the festival is a breeze; you can take the Metro-North Harlem Line to Brewster Station. Click here for MTA Metro-North’s schedule

    May 9, 2023

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