What to Do in the Hudson Valley This Weekend Oct 31 – Nov 2

Halloween spirit in the Hudson Valley is at its peak—equal parts spooky, sexy, soulful + spiritual. From forest masquerades to field recordings, haunted parades to candlelit mines, blacklight raves to Day of the Dead altars, the valley is alive with mystery, mischief, and magic this weekend. Take your pick below…

🏵️ Kingston, Fri Oct 31st, 12pm. Tibetan Buddhist Mandala Sand Painting Closing Ceremony at UPAC.
Tibetan Buddhist monks from Drepung Loseling Monastery are creating a Mandala sand painting all week long using millions of grains of colored sand. Free + open to the public—check viewing hours with a special closing ceremony on Friday. Info HERE.

👻 Woodstock, Fri Oct 31st, 4:30pm. Woodstock Halloween!
The Rock Academy Showband, a Halloween parade and a Time Warp flash mob take over the streets for a beloved town tradition where everyone—from kids to grown-ups—comes out to trick or treat! Info HERE.

👺 Big Indian, Fri Oct 31st, 3pm – late. Ralph’s Revenge: A Black Forest Masquerade at Urban Cowboy Lodge.
Ralph’s Bar & Bowling transforms into a lush, haunted forest where music, mystery + mischief collide for a night of feasting, dancing and spellbound revelry. Info HERE.

🐾 Kerhonkson, Fri Oct 31st, 5pm – 10pm. The 3rd Annual Halloween Pet Parade + Costume Contest at Starlite Motel.
A howling good time, shaking jams by @rust_records, killer pizza, spooky prizes, pet costume contest with raffles benefiting the Ulster County SPCA. Info HERE.

🧛 Congers, Fri Oct 31st, 6pm – 9pm. Halloween Costume Party at Red Barn Cidery.
Get ready for the Halloween party of the year! Adults only—leave the little ghouls at home. Dress to impress in your most wicked costume + compete for epic prizes. Info HERE.

🔦 Kingston, Fri Oct 31st, 7pm. Return of the “Night of the Living Voo!” at Keegan Ales.
Join THA VOO for their legendary Halloween Blacklight Party—costumes encouraged but never required! Info HERE.

🍺 Hudson, Fri Oct 31st, 8pm. 7 Kegs of Hell Halloween Party at Hudson Brewing Co.
Wicked live beats, spine-chilling costumes, and devilishly good drink specials to keep the night deliciously freaky! Info HERE.

🫦 Chatham, Fri Oct 31st, 8:30pm. The Rocky Horror Picture Show, with LIVE Local Shadow Cast at Crandell Theatre.
Celebrate the 50th Anniversary of the cult classic live! Don’t forget your umbrella. Info HERE.

⚰️ Kingston, Fri Oct 31st, 9pm – 2am. Crossing Over at Assembly.
A transformative two-floor Halloween dance party featuring immersive installations, a “graveyard” dance floor, electronic beats by Forfex, DJ Guy + DJ Jams Bond, interactive experiences exploring the spirit world, costume contests, and a safe, inclusive space to move, express, and connect with the community. Info HERE.

🦇Catskill, Fri Oct 31st, 9pm. ROBYN-O-WEEN at Avalon Lounge.
Get ready for ROBYN-O-WEEN with @therobynparty by @adventuresbk—dress to impress, compete for epic costume prizes, indulge in treats, and groove to a special performance by drag star Holly Samsonville! Info HERE.

🌲 Woodstock, Sat Nov 1st, 12pm. Listening to Land: Field Recording Workshop at Israel Wittman Sanctuary.
A field recording workshop with local sound artist Zaneta, inviting participants to connect with nature through attentive listening and ambient sound recording. Info HERE.

🐖 New Paltz, Sat Nov 1st, 1pm – 7pm. Pig Roast at Twin Star Orchards.
Peter’s roasted pulled pork marks the end of apple season—crispy, savory and perfect for sharing with friends and the community at the farm. Info HERE.

🔥 Woodstock, Sat Nov 1st, 5pm – 8pm. Day of The Dead: Dead Poets Open Mic Vegan Potluck Party at Shivastan Book Store, Art Gallery + Giftshop.
Gather around the bonfire for a cozy, inclusive open mic + sharing circle of creative poetry, music and spooky storytelling under the stars (or inside if it rains). Bring your favorite verses, snacks + good vibes for this soulful community celebration. Info HERE.

🕯️ Rosendale, Sat Nov 1st, 5:30pm – 8:30pm. HALLOWED: A Day of the Dead Masquerade + Candle Lighting at Widow Jane Mine.
Celebrate the true essence of Halloween with a candle lighting, ancestral altar + spirit masquerade honoring departed loved ones as the veil between worlds grows thin. Info HERE.

🦉Kingston, Sun Nov 2nd, 9am – 4pm. Red Owl Flea.
First Sundays every month through November 2nd—hunt for treasure with 20+ vintage sellers, local makers, antique dealers, upcyclers, pickers, collectors, food + more! Info HERE.

🎭 Rhinebeck, Sun Nov 2nd, 3pm. Misery at Rhinebeck Performing Arts.
Based on Stephen King’s novel, “Misery” follows a bestselling author whose rescue by an obsessed fan on a remote Colorado farm turns terrifying! Info HERE.

🎵 Woodstock, Sun Nov 2nd, 5pm. Twilight Kirtan at Shakti Yoga.
Raise your vibration with devotional chanting with Ishwari, Avinash + Alex. Stay tuned in to love and positivity. Info HERE.

🚜 Explore Hudson Valley’s vibrant SPRING to FALL Farmers Markets, Marketplaces, and Community-Shared Agriculture (CSA).
Support small local farms, foster a sense of community and promote healthy living. From live entertainment to family-friendly activities, they offer a fun and diverse experience for all! Info HERE.

Photo by Urana Kinlen

👉 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!