What’s Hot This Weekend: SparkHamptons Event Picks Oct.16-20, 2025

Hanks Pumpkin Town Corn Maze. Photo by Angela LaGreca

Spark Hamptons Event Picks: Oct. 16–20, 2025

Your guide to the best East End fall festivals, art shows, live music, and community events this weekend.

Thursday, Oct. 16
Boll & Branch Farm Stand at the Wölffer Wine Stand
Wölffer Estate Vineyard Wine Stand, 3312 Montauk Highway, Sagaponack, N.Y.
Oct. 16–17, noon–6 p.m.; Oct. 18, noon–7 p.m. (with live music)
A taste-and-texture pop-up at the Wölffer Wine Stand with a luxe outdoor lounge area through Oct. 18. Guests can relax, take home complimentary produce, and browse Boll & Branch bedding.

Friday, Oct. 17
Vanya and Sonia and Masha and Spike
Oct. 10–26 (Fridays–Saturdays, 7 p.m.; Sundays, 3 p.m.)
Southampton Cultural Center (scc-arts.org)
Christopher Durang’s hilarious play, directed by Bob Kaplan and produced by Boots on the Ground Theater, features Bonnie Grice, Randall Hemming, Alyson Reim, Shawn Friedman, Kristin Dougherty, and Leah Kerensky.
Click here for our Spark story on this production.

Innovators Talk Show
5:30–7:30 p.m.
Guild Hall, 158 Main St., East Hampton, N.Y. (guildhall.org)
A new conversation series spotlighting business and cultural leaders reshaping their industries. Hosted by Andrea Grover (executive director, Guild Hall) and Malcolm Carfrae (former executive at Calvin Klein and Ralph Lauren). The post-talk reception connects business owners, entrepreneurs, and community members.

Andrea Grover. Phot by Jessca Dalene. Malcolm Carfrae. Photo by BFA.

Masonic Music Series
Live jazz and social hour, 6:30 p.m.
Masonic Temple, 200 Main St., Sag Harbor (hamptonsjazzfest.org)

Saturday, Oct. 18
Shelter Island 26th Annual Fall 5K Run/Walk
11 a.m. Crescent Beach, Shore Road, Shelter Island, N.Y.
Kick off the weekend with one of the East End’s most beloved charity runs. This annual 5K in honor of Breast Cancer Awareness Month starts at Crescent Beach, rain or shine. All proceeds benefit women battling breast and gynecological cancers through local organizations, including the North Fork Breast Health Coalition, the Coalition for Women’s Cancers at Southampton Hospital, and Lucia’s Angels.

Shelter island Fall 5K Race/Walk supports women’s cancers on the East End. Photo courtesy of Shelter Island 5K.

LVIS 32nd Annual Landmarks Luncheon
11:30 a.m. The Maidstone Club, East Hampton, N.Y. (lvis.org)
The Ladies Village Improvement Society of East Hampton hosts its annual luncheon, featuring a discussion on the spirit and story of the historic neighborhood Freetown. Proceeds support LVIS community preservation projects.

Amber Waves Farm Oktoberfeast Fundraiser
2–5 p.m. Amber Waves Farm, Main Street, Amagansett, N.Y. (amberwavesmarket.com)
Celebrate the fall harvest season with farm-to-table food, live music, dancing, and family-friendly fun. Rain date: Oct. 19.

Amber Waves Farm Oktoberfeast. Photo courtesy of Jim Reed.

Sunset Theater Oktoberfest
2–7 p.m. Sunset Theater, 2 Brook Road, Westhampton Beach, N.Y.
Enjoy classic Oktoberfest fare—bratwurst, hot dogs, beer, cocktails, pumpkin decorating, and prizes—on the patio of Westhampton Beach’s newest movie theater. Great for families and beer lovers alike.

Pen to Paper: The Writing Table
3–5 p.m. The Baker House, 1650 Main Street, East Hampton, N.Y. (bakerhouse1650.com)
A mindful journaling workshop with Laura Rubin of AllSwell, dedicated to fostering creativity and supporting mental well-being. Perfect for creatives seeking a Hamptons wellness experience.

Pen To Paper Writing Workshop at The Baker House. Photo courtesy of Jim Reed.

Sunset Music – HooDoo Loungers
3 p.m. Wölffer Estate Vineyard Wine Stand, 3312 Montauk Highway, Sagaponack, N.Y.
Enjoy live outdoor music among the vines at one of the Hamptons’ most scenic wineries.

“The Worker” Gallery Opening
5–7 p.m. North Fork Arts Center, 211 Front St., Suite A, Greenport, N.Y. (northfork-artscenter.org)
A collaborative opening with OLA, the East End Latino-focused advocacy group, curated by Kelynn Alder. The exhibition explores the concept of “The Worker” and the full humanity of laborers. Proceeds benefit the artists, OLA, and the NFAC.

‘The Worker’ Art Exhibit. Photo courtesy of North Fork Arts Center.

“In Light of Tumbleweeds” – Art Show
5:30–7 p.m. (artist reception)
Greening Gallery, 26 Main Street, Sag Harbor, N.Y.
A Sag Harbor gallery favorite returns with a group show of contemporary painters capturing the quiet beauty of the Hamptons after summer. Featuring Viktor Butko, Amy Florence, Rolf Hellem, Mathias Meinel, and Melissa Franklin Sanchez.

The Joni Project – Celebrating the Music of Joni Mitchell
8 p.m. Bay Street Theater, 1 Long Wharf, Sag Harbor, N.Y. (baystreet.org)
A live concert tribute to Joni Mitchell’s iconic songs, led by Katie Pearlman and her band. A must-see for Hamptons music lovers.

‘The Joni Project’. Photo courtesy of Bay Street Theater

CSNY Tribute Band Four Way Street
8 p.m. The Stephen Talkhouse, 161 Main Street, Amagansett, N.Y. (stephentalkhouse.com)
Rock out to the classics of Crosby, Stills, Nash & Young performed by tribute band Four Way Street at this legendary East End venue.

Sunday, Oct. 19
Cab Franc Forward Winemaker’s Dinner
The Pridwin Hotel, 81 Shore Road, Shelter Island, N.Y. (caperesorts.com/pridwin)
A luxurious multi-course dinner on the water-view terrace celebrating New York State’s signature red wine, Cabernet Franc. Menu by Executive Chef Todd Ruiz, served at a communal table for 50 guests.

Monday, Oct. 20
East Hampton Town Candidates Debate
6 p.m. LTV Studios, 75 Industrial Road, Wainscott, N.Y. (ltveh.org)
Stay informed and engaged with this live debate featuring candidates for East Hampton Town Clerk and Town Board. Moderated by Joe Shaw, executive editor of the Express News Group.

Notable Art Shows on the East End

“Second Skin,” curated by Estrellita B. Brodsky
Through Dec. 28
Southampton Arts Center, 25 Jobs Lane, Southampton, N.Y. (scc-arts.org)
This acclaimed exhibition explores how fashion functions as art, politics, power, and personal armor. A must-see for art and fashion lovers visiting the Hamptons this fall.

Felix Beaudry. ‘Bury Me In Your Tits’. ‘Second Skin’ show, courtesy of Southampton Arts Center.

“4 Artists, Higher Vision Shaping Form”
Julie Keyes Art, 45 Main Street, Sag Harbor, N.Y.
Walter Bobbie, Judith Henriques-Adams, Dwight Ripley, and Sumayyah Samaha exhibit abstract works that push artistic boundaries in Sag Harbor’s vibrant art scene.

Walter Bobbie. 4 Artists Higher Vision Shaping Form. Photo courtesy of Julie Keyes Gallery

Jonathan Nash Glynn – Solo Exhibition
Through Oct. 26. Open 11 a.m.–3 p.m.
New Space, Bridgehampton Museum, 2368 Montauk Highway, Bridgehampton, N.Y. (bridgehamptonmuseum.org)
Large-scale acrylic paintings inspired by the Hubble and Webb space telescopes. Presented with the Hamptons Observatory, including a public stargazing experience.

The Banned Book Project Art Exhibit
Through Oct. 30
Springs Library, 1 Parson Place, East Hampton, N.Y. (springshistoricalsociety.org)
East Hampton Library, 159 Main Street, East Hampton, N.Y. (easthamptonlibrary.org)
Curated by Karyn Mannix, this group show highlights the power of literature and the increasing threat of censorship.

Karyn Mannix. ‘Banned Book Project’. Photo courtesy of Karyn Mannix