2026 Editor’s Picks: What to Do in the Hudson Valley on Memorial Day Weekend!

Memorial Day Weekend in the Hudson Valley carries its own rhythm — small-town parades, live music drifting through the fields, wineries buzzing, and neighbors gathering across towns + villages. It’s also a time to honor those who served while reflecting on the spirit of community, inclusiveness and belonging that continues to shape The Valley. Hot List below…

🗓️ ALL WEEKEND

🏇 Pine Plains, Fri – Sat. Opening Weekend: Polo Matches + Classes at Mashomack Polo.
Spend a day in the countryside watching fast-paced polo matches, taking lessons + enjoying one of the Hudson Valley’s most scenic sporting traditions. Info HERE.

🍀 East Durham, Fri – Sun. Irish Festival at Michael J. Quill Irish Cultural & Sports Center.
Celebrate Irish music, culture, heritage, performances, food + more. Info HERE.

🍷 Chatham, Sat + Sun, 11am – 6pm. Hudson Berkshire Wine & Food Festival at Columbia County Fairgrounds.
A weekend-long tasting experience featuring artisanal wines + hard ciders alongside regional food vendors, set for a full day of sipping, sampling + seasonal celebration. Info HERE.

🎨 New Paltz, Sat – Mon. Woodstock-New Paltz Art & Crafts Fair at Ulster County Fairgrounds.
Check out hundreds of artists + makers across multiple mediums alongside live music, craft demonstrations, specialty food + drinks, and family-friendly activities. Info HERE.

🎸 Warwick, Sat – Mon. Bob Dylan Tribute Festival at Warwick Valley Winery & Distillery.
Come celebrate the music of a legend with The Bobcats, The Mammals, Dylan Doyle Band + more! Info HERE.

🌺 Hudson Valley, All weekend! Your Ultimate Guide to the Hudson Valley’s Vibrant Farmers Markets: Spring to Fall.
Your go-to guide to the Hudson Valley’s vibrant Farmers Markets, spring through fall—where fresh seasonal produce, local farms and community come together. Info HERE.

🗓️ Friday, May 22

🍎 Walden, 5pm – 8pm. Karaoke Night at Angry Orchard Cider House.
A laid-back evening of crowd-favorite sing-alongs where anyone can grab the mic, plus Angry Hour drink specials, cider + bites, and a fun, no-pressure vibe built for laughs + community. Info HERE.

🎸 Woodstock, 7pm. Bob Dylan Birthday Party with The Bob Cats at Colony Woodstock.
Woodstock’s premier Dylan tribute band channels the spirit of the Rolling Thunder Revue with a high-energy night of classic songs, deep cuts + rock ’n’ roll fire led by drummer Jerry Marotta + an all-star local lineup. Info HERE.

🎸 Beacon, 7pm – 11pm. 90’s Live Band Karaoke Party at Broadway in Beacon.
Belt out 90s hits all night with a live band, plus an & JULIET Broadway ticket raffle, costume contest, special appearances + high-energy surprises. Info HERE.

🗓️ Saturday, May 23

🥾 Haines Falls, 10am. Historic Catskills Railroad Hike at North-South Lake.
Mountain Top Historical Society’s guided hike exploring the forgotten railroads that once carried travelers to the grand Catskills resorts, with stops at former stations, rail beds + surviving historic artifacts. Info HERE.

🍷 Montgomery, 11am – 5pm. Bud Break: Spring Wine Festival at City Winery Hudson Valley.
Kick off spring with a full-day wine celebration featuring new seasonal releases, curated tasting pairings, live music, lawn games + the opening of the outdoor wine garden overlooking the vineyard. Info HERE.

🎧 Woodstock, 12pm – 5pm. 3rd Annual Woodstock Vinyl Slam at Station Bar & Curio.
Multiple tri-state vinyl dealers gather under the covered patio spinning rarities + gems with DJ Sean McDevitt—alongside all-day rare records crate digging. Info HERE.

🦋 Margaretville , 2pm – 3:30pm. Puppet Making Workshop + “Mariposa Butterfly” at The Open Eye Theater.
A bilingual Spanish + English children’s performance with a butterfly puppet-making workshop followed by a moving story of two neighbors finding connection through wonder, loss + shared understanding. Info HERE.

🎪 Kingston, 8pm. Hudson Valley Burlesque Bash: Circus of Tease at Assembly.
A high-energy night of burlesque, sideshow acts like sword swallowing + bed of nails, comedy, drag, acrobatics + aerialists, all capped with a DJ dance party + surprise pop-up performances. Info HERE.

🗓️ Sunday, May 24

🇺🇸 Fleischmanns, 10am – 4pm. Memorial Day Street Fair on Main Street.
A lively Catskills street fair celebrating local makers, food, live entertainment + family-friendly activities in the heart of the historic mountain village. Info HERE.

🪕 Woodstock, Sun May 24, 12pm – 6pm. Bearsville Bluegrass Festival at Bearsville Park.
A lively day of bluegrass performances, local food and drink, artisan vendors, and family-friendly fun set in a scenic outdoor park. Info HERE.

🎶 Rosendale, 4pm – 10pm. Gratefully Yours Band’s Family Picnic at Widow Jane Meadows.
A laid-back meadow gathering with live music, sunset vibes + plenty of space to spread out with blankets, chairs, coolers + friends. Info HERE.

🎺 Kingston, 8pm – 10pm. Sekanjabin + MacNCheez Balkan Power Trio at Tempo.
An explosive night of global fusion as 11+ piece ensemble Sekanjabin (on tour from Istanbul) blends Turkish folk roots with salsa, flamenco, reggae, calypso + more, alongside MacNCheez Balkan PowerTrio’s high-energy dance grooves. Info HERE.

🗓️ Monday, May 25 (Memorial Day)

A day of parades, ceremonies and reflection unfolds across the Mid-Hudson Valley this Memorial Day, with communities coming together to honor those who served. Here is a short list below:

📍DUTCHESS COUNTY – Info HERE.

🇺🇸 Amenia + Dover Plains, 11am. Memorial Day Ceremony at Fountain Square / Bank of Millbrook (Rt 22).

🇺🇸 Beacon, 11am. Memorial Day Ceremony at Veterans’ Memorial Hall.

🇺🇸 Hyde Park, 10am. Memorial Day Parade + Ceremony from  Albany Post Road to Town Hall & War Memorial.

🇺🇸 Millbrook, 11am. Memorial Day Parade + Ceremony at Franklin Ave & Tribute Gardens Park.

🇺🇸 Millerton, 10am. Memorial Day Parade + Ceremony at Veterans Park.

🇺🇸 Pine Plains, 10:30am. Memorial Day Parade + Ceremony on Main St.

🇺🇸 Poughkeepsie, 11am. Memorial Day Ceremony at Dutchess County War Memorial.

🇺🇸 Red Hook, 9:15am. Memorial Day Parade + Ceremony at Veterans Memorial Park.

🇺🇸 Rhinecliff, 9am. Memorial Day Parade from Old School House to the Center of Town.

🇺🇸 Tivoli, 10am. Memorial Day Ceremony at Monument Hill on Broadway.

🇺🇸 Wappingers Falls, 11am. Memorial Day Ceremony at 8 School St.

📍OTHER LOCATIONS IN THE HUDSON VALLEY

🇺🇸 Catskill, 1:30pm. Memorial Day Ceremony on Water Street at the Courthouse. Info HERE.

🇺🇸 Hudson, 10am. Memorial Day Parade at 7th St Park. Info HERE.

🇺🇸 Hurley, 10am. Memorial Day Parade + Ceremony at Zandhoek Road to Hurley Town Hall. Info HERE.

🇺🇸 Kingston, 1pm. Memorial Day Ceremony at Kingston Hall. Info HERE.

🇺🇸 Newburgh, 10am. Memorial Day Parade at West Street to Broadway + Services at Washington’s Headquarters. Info HERE.

🇺🇸 Rosendale-Tillson, 10am. Memorial Day Parade + Ceremony from Tillson Firehouse to Veteran Memorial Park. Info HERE.

🇺🇸 Woodstock, 12pm. Memorial Day Parade + Ceremony from the Woodstock Playhouse to Woodstock Cemetery and end at Neher Street. Info HERE.

Photo by Urana T. Kinlen of Overlook Mountain from the Woodstock Land Conservancy’s Zena Cornfield Preserve, May 2026.

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Be sure to visit our Event Calendar HERE for more amazing happenings in the Hudson Valley.

Have a wonderful weekend from Inside+Out Upstate NY!