2026 Editor’s Picks: What to Do in the Hudson Valley on Jun 19 – Jun 21

Summer Solstice, Father’s Day and Juneteenth mark a weekend of gatherings across the Hudson Valley. A stretch of early summer days moving between remembrance, celebration, and the longest light. Hot List below…

ALL WEEKEND 

📜 Kingston, Fri + Sat. 8th Annual Juneteenth Celebration at Harambee Kingston.
A two-day commemoration featuring a Freedom Walk, historic reburial ceremony, monument unveiling + a community festival with live music, art, drumming, vendors + cultural programming. Info HERE.

🐕 Kerhonkson, Fri – Sun. World Cup + Dog Day Fundraiser/Craft Fair at Rough Cut Brewing.
World Cup watch parties, dog rescue fundraiser with local vendors + craft fair events throughout the weekend. Info HERE.

🎭 Catskill, Fri – Sun. The Laramie Project at Bridge Street Theatre.
A powerful documentary play exploring identity, compassion + the lasting impact of hate through the words and stories of a community. Info HERE.

☀️ Woodstock, Sat + Sun. Full Spectrum Summer Solstice at Mountain View Studio.
On the longest days of the year, we gather to awaken, create + radiate — a full-spectrum weekend of nature walk & Qigong, Kundalini yoga, sound healing, ecstatic art-making + sauna flow. Come for one day or both. Sliding scale. Open to all levels. Info HERE.

🍇 New Paltz, Sat + Sun. Father’s Day Weekend at Robibero Winery.
Treat Dad to wine, bourbon, craft beer, wood-fired pizza, live music, cornhole + fire-pit hangs all weekend long. Family + pet friendly. Info HERE.

🎶 Woodstock, Sat + Sun. West Side Story at The Woodstock Playhouse
One of the greatest love stories of all time! Get Tickets HERE

🌙 High Falls, Sat + Sun. Summer Solstice: Telepathy and the Dream World.
A weekend workshop exploring dreams, intuition, lucid dreaming, plant meditations + nature-based practices. Info HERE.

🍷 Warwick, Sat + Sun. Sangria Weekend at Applewood Winery.
Enjoy house-made sangria flights, live music, food specials + relaxed summer vibes all weekend long. Info HERE.

🍺 Round Top, Sat + Sun. Bavarian Summer Fest at Nussy’s Bier Garten.
A weekend of live German music, dancing, food + beer garden celebrations in the Catskills. Info HERE.

🥾 Catskills, All Year. Catskills Fire Tower Challenge.
Hike to all eight Catskill fire towers, including the newly added Mount Utsayantha + Bramley Mountain towers, and experience some of the region’s most rewarding views. 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, JUNE 19

🎬 Woodstock, 4pm. With Peter Bradley Film Screening + Evening with the Filmmaker at Byrdcliffe Theatre.
A screening of the acclaimed documentary followed by a conversation with the filmmaker. Info HERE.

🔥 Beacon, Fri 5pm – 10pm. “Saints & Sinners” Summer Solstice Night Market at Prophecy Hall.
An immersive solstice gathering of art, ritual, live performance, fire + curiosities in a candlelit, transformed space. Info HERE.

SATURDAY, JUNE 20

🍗 Poughkeepsie, 1pm – 5pm. City of Poughkeepsie Juneteenth Celebration at Waryas Park.
Live music, vendors, food and a parade at 12:30pm. Info HERE

🌞 Saugerties, 2pm. Summer Solstice Carnival at Spiral House Park.
A family-friendly solstice gathering with live music, art, games, workshops, food + playful performances celebrating the longest day of the year. Info HERE.

🎶 Kingston, Sat 2pm–11pm. The Down County Jump at TEMPO Performing Arts Center.
A Summer Solstice celebration of eclectic live music, dancing + community gathering. Info HERE.

🐎 Pine Plains, 4pm. 27th Annual Mashomack International Polo Challenge at Mashomack Polo Club.
An afternoon of world-class polo followed by dinner + dancing under the tent. Info HERE.

💃 Copake, 7pm – 9pm. Summer Dance Party at Copake Grange.
Celebrate the start of summer with dancing, refreshments + community fun. Free; donations and food pantry contributions welcome. Info HERE.

🎶 Saugerties, 8pm. Summer Solstice: Desert Blues with Nour Harkati at Opus 40.
North African rhythms, desert blues + global sounds performed in the quarry. Info HERE.

🏃 Poughkeepsie, 7pm. Chasing Daylight 5K at Walkway Over the Hudson.
A sunset 5K supporting Hudson Valley nonprofits while crossing one of the region’s most iconic landmarks. Info HERE

SUNDAY, JUNE 21

⛵️ Croton-on-Hudson, 10am – 9pm. Hudson River Music Festival at Croton Point Park.
Celebrate Father’s Day with a full day of music, community + activism inspired by the legacy of Pete Seeger + Woody Guthrie, with headlining performances by Jesse Welles and performances along the Hudson River as America approaches its 250th anniversary. Info HERE.

⚾ Kingston, 1pm. Vintage Base Ball: Kingston Guards vs. Rip Van Winkle Base Ball Club at Herzog’s Field.
Step back to 1864 with vintage rules, period uniforms + old-fashioned baseball fun for the whole family. Free admission. Info HERE.

🌞 Catskill, 4pm – 8pm. Catskill Summer Solstice on Main Street.
Celebrate the longest day of the year with live music, dancing, crafts, workshops, family activities, food vendors + community happenings throughout downtown. Info HERE.

🎸 New Windsor, 5pm – 9pm. Black Country, New Road with Horsegirl at Storm King Art Center.
An outdoor concert pairing two acclaimed indie acts in the sculpture park. Info HERE.

Photo by Catskill Center of the Bramley Mountain Firetower in Delhi NY. The 2026 Catskills Fire Tower Challenge adds two new towers in Delaware County, inviting hikers to visit all eight historic Catskill fire towers through the end of the year.

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