SouthamptonFest Returns for 10th Year This Weekend

Stiltwalker and Jester Jim group at SouthamptonFest
Stiltwalker and Jester Jim group at SouthamptonFest
Dennis Bontempo, Ron Esposito, Julie Fitzgerald

After a two-year hiatus (same old pandemic story), SouthamptonFest is returning for its 10th year, attracting locals and visitors for a weekend of arts, crafts, dance, live music, pumpkin carvers, children’s activities, the popular chowder contest — and more.

Take a look at everything that’s happening in Southampton Village this weekend and plan accordingly.

What to Do at SouthamptonFest 2022

SouthamptonFest Chowder Contest
SouthamptonFest Chowder ContestDennis Bontempo, Ron Esposito, Julie Fitzgerald


SouthamptonFest weekend begins with a high-energy Southampton Rotary Kickoff Party in Agawam Park (51 Pond Lane) — a gathering of old and new friends with live music by Coverland, complimentary beer and wine from 6:30–8:30 p.m., followed by a cash bar until 9:30 p.m,, along with food from local food trucks. Tickets are $30 per person in advance at ($40 at the door).


The festivities truly get underway on Saturday as an all-day celebration with happenings throughout Southampton Village. Musical acts such as Next Level Reggae Band and Gene Casey and The Lone Sharks will perform in Agawam Park, where food fans can also enjoy the popular annual Chowder Contest featuring entries from local restaurants and caterers from noon–2 p.m. (winner announced at 3:50 p.m.), and food trucks will offer tasty eats. Additional musical performances will take place on Main Street.

Also in Agawam Park, experience salsa dancing lessons and demonstrations for all ages and abilities from Cuban salsa teacher Jamie Ruiz from 2:30–4 p.m., and kids’ activities such as Jester Jim performances at 2 p.m. and 3:30 p.m. (and 12:30 p.m. on the steps of Southampton Arts Center). Face painting and balloon animals are also in the park from 11 a.m.–4 p.m. And the Maniac Pumpkin Carvers won’t fail to impress as they create unique and often remarkably photorealistic pumpkin designs, carved live all day (11 a.m.–6 p.m.) in the park.

The Maniac Pumpkin Carvers at work! SouthamptonFest
The Maniac Pumpkin Carvers at work!Tom Kochie

Meanwhile, Southampton Village restaurants will welcome residents and visitors with fall-themed specials. And an Art + Design Crawl will feature some of the best design shops and art galleries in town from 11 a.m.–4 p.m., and participants can enter a raffle to win some great prizes. As the Crawl concludes at 4 p.m. on Saturday, Oscar Molina Gallery (28c Jobs Lane) is hosting an artists’ talk with Darlene Charneco and Alex Vignoli about their Charneco / Vignoli: Visible Language exhibition, which is closing on Monday, October 3. This event is not officially part of SouthamptonFest, but it coincides perfectly with the day’s activities.

Topiaire Flower Shop (51 Jobs Lane) is putting together colorful, eye-catching Thanksgiving tablescapes during a live demonstration with fresh flowers and organic materials from 11 a.m.–noon.

Local not-for-profit organization the Southampton Artists Association is showcasing work by local professional and amateur artists to for festival goers to admire and/or purchase all day (11 a.m.–4 p.m.) on Saturday and Sunday in Agawam Park.

Southampton African American Museum (245 North Sea Road) is inviting guests to experience a digital tapestry and exhibit, Grooming a Generation: A History of Black Barbershops & Beauty Parlors, from 11 a.m.– 3 p.m. with an augmented reality tour celebrating the long and storied history of barbering in the African American community.

Rogers Mansion in Southampton
Rogers Mansion in SouthamptonOliver Peterson

Southampton History Museum (17 Meeting House Lane) will open its doors and grounds to guests looking for spooky delights from 11 a.m.–4 p.m. on Saturday. Experience the horrors of a haunted Gilded Age mansion as Ghosts, Goblins and Ghouls inhabit the historic rooms of the Rogers Mansion, which dates back to 1650. The museum’s 10 historic outbuildings will also be open and “occupied with the unimaginable,” including Creatures in the Carpenter’s Shop, Devils in the Decoy Shed and Bad Barnaby in the Blacksmith Shop.

Among other highlights this year, the Southampton Arts Center (25 Jobs Lane) exhibit A Celebration of Trees is open to the public from 6–8 p.m. The show features artists such as Freeman Vines, Beth Moon, Frank Relle, Charles Gaines, Sebastião Salgado and Nicholas Herrara, as well as a pair of special outdoor performances by musician Tom Wall, who will interact with centuries-old trees at 3 p.m. and 6 p.m.

The Southampton Cultural Center (25 Pond Lane) is holding their sixth annual An Evening of Wine and Roses Gala, a ticketed event (available at, from 6–10 p.m. with dinner, good wine, refreshing cocktails, live entertainment and a silent auction.

Face painting at SouthamptonFest
Face painting at SouthamptonFestDennis Bontempo, Ron Esposito, Julie Fitzgerald


On Sunday, the Southampton Chamber of Commerce Farmers and Artisans Market will take place in Agawam Park from 9 a.m.–3 p.m. (And don’t forget to view the Southampton Artists Association artwork in the park!)

The 10th annual SouthamptonFest is a wonderful weekend of fun for adults and children to experience and enjoy Southampton Village and all it has to offer. Participate as much or as little as you want!

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