Top Hamptons Events This Weekend: Film Festival, Fall Festivals, Dog Walks and More, Oct. 8-12

Hollywood stars, Montauk’s chowder contest, Wölffer’s Harvest Party, ARF’s Dog Walk and Judy Carmichael lead a weekend of music, art, food and community events.

The Hamptons International Film Festival heads into its final five days, Montauk breaks out the chowder, and Wölffer celebrates the grape harvest. Add live jazz, community fundraisers and sidewalk sales in Sag Harbor and Westhampton Beach, and Columbus Day weekend has plenty going on.

Here are Spark Hamptons’ picks for Oct. 8-12.

EDITOR’S TOP 5

1. Hamptons International Film Festival

Thursday, Oct. 8-Monday, Oct. 12 | Various times and ticket prices

East Hampton, Sag Harbor and Southampton

Jesse Eisenberg, Ron Howard, John Turturro in conversation at the HIFF

Jesse Eisenberg, Pedro Pascal, Sara Bareilles and John Turturro are among the stars on screen during the festival’s final five days. Ron Howard’s Richard Avedon documentary, a Bob Balaban tribute and a star-studded closing night are also on the schedule. See Spark’s full guide.

See our HIFF Highlights and picks here.

2. ARF Dog Walk to the Sea

Saturday, Oct. 10 | 9 a.m.-noon | $40-$250; children under 10 free with a registered adult

Mulford Farm, 10 James Lane, East Hampton

Hundreds of dogs and their humans head to Main Beach for ARF’s annual fundraiser, with pet contests, vendors, giveaways and a silent auction. The four-legged participants are the stars.

3. Montauk Fall Festival and Clam Chowder Contest

Saturday, Oct. 10, and Sunday, Oct. 11 | 11 a.m.-5 p.m. | Free admission

Montauk Town Green, 743 Montauk Highway, Montauk

Montauk Fall Festival. Photo: Montauk Chamber of Commerce

Montauk’s 45th annual Fall Festival brings live music, food, vendors and family activities to the village green. Saturday’s clam chowder contest starts at 11 a.m., with tasting mugs on sale at 10 a.m.

The festivities continue Saturday night with the inaugural Montauk Comedy Festival, featuring stand-up performers from the Long Island Comedy Festival at the Montauk Playhouse, 240 Edgemere St., at 8 p.m. Tickets are $43.

Comedy tickets to Montauk Comedy Festival, here. 

4. Wölffer Estate Annual Harvest Party

Saturday, Oct. 10 | Noon-4 p.m. | Adults $205; ages 2-20 $105; children 2 and under free with ticket

The Wine Stand at Wölffer Estate, 3312 Montauk Highway, Sagaponack

Wölffer Estate Annual Harvest Party

Grape-stomping, barrel-rolling, hayrides, live music and food and wine stations make this a signature harvest celebration. Advance tickets required; rain date Sunday, Oct. 11.

Website:

5. Judy Carmichael Trio at Bay Street Theater

Saturday, Oct. 10 | 8 p.m. | $44-$56

Bay Street Theater, Sag Harbor

Judy Carmichael Trio at Bay Street Theater

Grammy-nominated jazz pianist and vocalist Judy Carmichael returns with guitarist John Merrill and saxophonist and clarinetist Dan Block for an evening of stride piano, swing and Great American Songbook favorites.

FALL FESTIVALS, FOOD & SHOPPING

Sag Harbor Columbus Day Weekend Sidewalk Sale

Saturday, Oct. 10-Monday, Oct. 12 | 9 a.m.-8 p.m. listed | Free

Main Street and surrounding streets, Sag Harbor

Sag Harbor Columbus Day Weekend sidewalk sales

Village merchants bring clothing, accessories, gifts and more outdoors for three days of holiday weekend bargains.

Website:

Springs Food Pantry’s 8th Annual Chowdah Chowdown

Saturday, Oct. 10 | Noon-3 p.m. | $50 plus fee

Springs Tavern and Grill, 15 Fort Pond Blvd., Springs

Sample chowders and soups from East End chefs, vote for your favorites and enjoy music and raffles while supporting Springs Food Pantry.

Westhampton Beach Fall Festival and Sidewalk Sales

Fall Festival: Saturday, Oct. 10, 11 a.m.-5 p.m. | Sidewalk sales: Saturday, Oct. 10-Monday, Oct. 12 | Free

Main Street, Sunset Avenue and Maria Z. Moore Community Park, Westhampton Beach

Westhampton Beach side walk sales and more this weekend

Live music, food trucks, artisan vendors and family activities fill downtown Saturday, while village retailers offer holiday weekend deals. Festival rain date Sunday, Oct. 11.

Oktoberfest at Solé East

Sunday, Oct. 11 | 3-9 p.m. | Cash bar

Solé East, 90 Second House Road, Montauk

German food, beer steins, a DJ and a live oompah band bring Oktoberfest to Montauk, with a portion of proceeds benefiting the Montauk Food Pantry.

ART & CULTURE

Lynn Matsuoka: The World of Sumo

Saturday, Oct. 10 | Artist talk 12:30-1 p.m.; reception 1-3 p.m.

Stella Flame Gallery, 2385 Main St., Bridgehampton

Artist Lynn Matsuoka discusses her decades documenting Japan’s sumo wrestlers and the extraordinary access behind her work. A reception follows.

Website:

In Conversation With Artist Irina Alimanestianu

Saturday, Oct. 10 | 4:30-6 p.m.

Keyes Art, 45 Main St., Sag Harbor

Irina Alimanestianu, Flesh and Bark, What Touches, 2026 at Julie Keyes Art, Sag Harbor

Artist Irina Alimanestianu discusses paintings that weave together landscape, memory, mythology and history.

Storytellers: An Oral History of the Historic Black Beachfront Communities

Sunday, Oct. 11 | 2-4 p.m. | General admission $10; members $5

The Church, 48 Madison St., Sag Harbor

Donnamarie Barnes collection.

Residents and descendants share the history of Sag Harbor’s Black beachfront communities, including Azurest and Sag Harbor Hills, in a program connected to The Church’s Dear Mazie exhibition.

BENEFITS & COMMUNITY

Inlet2Inlet Beach Cleanup & Fall Fair

Saturday, Oct. 10 | Cleanup 11 a.m.; Fall Fair noon-5 p.m.

Dune Road shoreline; Fall Fair at the Great Lawn, 35 Main St., Westhampton Beach

Inlet2Inlet beach cleanup this weekend

Help clean the beaches between Moriches and Shinnecock inlets, then enjoy music, food and family activities at the Fall Fair. Rain date Sunday, Oct. 11.

Shinnecock Community Jewelry Fundraiser and Music Hour

Saturday, Oct. 10 | Noon-6 p.m.; music 4-5 p.m. | Music hour $20

Unitarian Universalist Meeting House, 977 Bridgehampton-Sag Harbor Turnpike, Bridgehampton

Shop jewelry supporting Shinnecock community housing initiatives, with live music by the Thunderbird Sisters, Meegan Chaskey, Abby Flemming and others.

No Matter What 5K Run/Walk

Sunday, Oct. 11 | 9 a.m. start, rain or shine | $44.15

Two Mile Hollow Beach, East Hampton

Two Mile Hollow Beach. Photo by Angela LaGreca

Hamptons Run Club hosts a 5K supporting local mental health programs, with music, cash prizes and a Lululemon T-shirt for the first 100 registered participants.

Angela LaGreca

Editor, Co-Founder/Publisher

Angela LaGreca, Editor-in-chief and co-Founder/Publisher of Spark Hamptons, is a four-time Emmy Award-winning journalist, producer, writer and comedian/host. Her TV credits include NBC’s “Today,” ABC’s “The View,” and, most recently, the primetime cable news program “Cuomo” on NewsNation. On the East End, she was the Creative Director at LTV, VP Features/Events/Photo Editor at Dan’s Papers, and has performed at Guild Hall, Bay Street Theater and the WHBPAC. Her publishing career began at Modern Photography, where she was managing editor. LaGreca lives in Manhattan and East Hampton and can be reached at angelatvmedia@gmail.com and angela@sparkhamptons.com .