What to Do in the Hudson Valley This Weekend Dec 19 – Dec 21

Celebrate the Winter Solstice and the season with lantern walks, live music, thoughtful rituals, stargazing, holiday feasts, family fun, and plenty of ways to gather—indoors and out. Take your pick below…

⛄️ Newburgh, Fri Dec 19th – Sun Dec 21st. Newburgh Frost Fest.
Winter Solstice Lantern Walk—create lanterns, hot chocolate, and a magical community walk to celebrate the light during the darkest nights of the year. Ornament + Menorah Making, Santa Fun Run + Food Drive and more! Info HERE.

🍣 Hyde Park, Fri Dec 19th + Sun Dec 21st, 12pm + 1:30pm. Holiday Sushi Omakase Pop-up Lunch at Dassai Blue.
An authentic omakase-style experience featuring a refined nine-course tasting, with optional Dassai Blue pairings for a memorable meal. Info HERE.

❓Walden, Fri Dec 19th, 6pm – 8pm. Holiday Movies Trivia Night at Angry Orchard.
A festive night of holiday movie trivia, tacky outfits, cider on draft, food, drink specials, and prizes. Info HERE.

🍻 East Fishkill, Fri Dec 19th, 6:30pm – 9pm. LGBTQ+ Speed Dating + Comedy at Sloop Brewing Co.
Unhinged Dating Upstate hosts a hilarious speed-dating night with comedy, flirty holiday rounds, and cozy mingling—festive, unhinged attire encouraged. Info HERE.

🎸 Bearsville, Fri Dec 19th, 8pm. Rhett Miller and the All-Stars Holiday Party at Bearsville Theater.
Performing “A Lifetime of Riding by Night,” a deeply personal album shaped by surrender, reflection, and trust, showcasing some of his most unguarded songwriting to date. Read more about Rhett Miller. Info HERE.

🎅 Red Hook, Sat Dec 20th, 12pm 12pm – 3pm. Christmas in the Village.
A free holiday celebration for children ages 0–14 featuring festive crafts, treats and hot chocolate, a new toy for every child, and a special visit from Santa. Info HERE.

🌒 Hudson, Sat Dec 20th, 1pm – 5pm. Olana Winter Solstice Celebration.
Celebrate the changing seasons at Olana with a free community day featuring winter activities, seasonal artmaking, house exploration, snow science, and a visit with Hank the miniature donkey. Info HERE.

🔭 Saugerties, Sat Dec 20th, 3pm – 7pm. Winter Solstice Celebration at Opus 40.
Take winter walks + make a solstice lantern, Bard College choral performances, bonfire, drinks + snacks, astrology mini-readings, meditative luminary procession and end the evening with community stargazing with the Hudson Valley Astronomical Association. Info HERE.

💚 Hudson, Sat Dec 20th, 3pm – 5pm. Kwanzaa Celebration at Hudson Hall.
Celebrate Kwanzaa with an afternoon of family-friendly arts and crafts, dancing, drumming, a candle-lighting ceremony, and the sharing of the Nguzo Saba, honoring African-American culture, unity, and heritage. Info HERE.

🎬 Saugerties, Sat Dec 20th, 3pm – 5pm. Woodstock Film Festival presents: “Is this thing on?” at Upstate Films.
An encore screening (free, RSVP required) follows a couple navigating love, identity, and co-parenting amid divorce and the New York comedy scene. Info HERE.

❄️ Tannersville, Sat Dec 20th, 4pm – 5:30pm. Winter Solstice Forest Bathing + Luminary Walk at Mountain Top Arboretum.
A guided winter forest walk exploring the season, followed by a tea ceremony and a luminary-lit return path, marking the solstice as a time of renewal; the walk is under one mile on easy to moderate terrain. Info HERE.

🕎 Copake, Sat Dec 20th, 5pm – 7:30pm. 2nd Annual Hanukkah Party at Copake Grange.
Gather together for a potluck dinner with candle lighting, songs, and other festive activities. Open to the whole community. Reservations required. Info HERE.

🌟 Beacon, Sat Dec 20th, 8pm – 11pm. The Slambovian Circus of Dreams at Towne Crier Cafe.
A rootsy, psychedelic holiday show with twisted carols, original tunes, and an offbeat, joy-sparking spirit perfect for celebrating with family + friends. Info HERE.

🎼 Hudson, Sun Dec 21st, 9:30am – 11:30am. Solstice with Grace Woodard at Pocketbook Hudson.
Grace Woodard leads a free, solstice-focused Deep Listening® workshop exploring sound, mindfulness, and collective creativity. Info HERE.

🎅 Kingston, Sun Dec 21st, 10am brunch with Santa + Ice Skating at The Cornell.
A magical holiday brunch with photos with Santa, a DIY hot chocolate station, an open ice rink, and festive waterfront vibes for the whole family. Info HERE.

🌒 Woodstock, Sun Dec 21st, 11am – 6pm. Shining Solstice Celebration at Mountain View Studio + Woodstock Community Center.
A day of Kundalini yoga, gong, nature, and a Satsang dinner inviting you to pause and reflect at the winter solstice—open to all levels, with options to join the class or stay for the full experience. Info HERE.

🎄Woodstock, Sun Dec 21st, 7pm – 10pm. A John Prine Christmas at Colony.
A special holiday tribute to John Prine featuring fresh takes on classics, deep cuts, and seasonal favorites, with performances by local musicians and a portion of proceeds benefiting the Hello In There Foundation. Info HERE.

👩‍🌾 Explore the Bounty of Winter at Hudson Valley Farmers Markets + CSAs
These cozy seasonal pop-ups turn cold-weather weekends into lively celebrations of local food, makers and culture! 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!