Stonington Vineyards Pairs a Fall Weekend With Pizza, Wine and Live Music
Stonington Vineyards Pairs a Fall Weekend With Pizza, Wine and Live Music on Oct. 10 and 11, turning two October afternoons into relaxed fall pop-ups among the vines with wood-fired pizza on Saturday and acoustic performances from Brandon Donahue and Brad Bensko across the weekend.
The winery’s Fall Pop-Up series is intentionally more casual than its ticketed summer concert nights. There is no admission charge or ticket requirement. Visitors can stop in, buy a tasting, glass, or bottle of Stonington Vineyards wine and settle in for an afternoon overlooking the vineyard.
This weekend brings something different each day.
Saturday: Brandon Donahue and G Pa’s Fired Pizza
Brandon Donahue performs Saturday from 2 to 5 p.m., while G Pa’s Fired Pizza brings its mobile wood-fired pizza operation to the vineyard.
Donahue is part of southeastern Connecticut’s busy local live-music circuit and isn’t new to Stonington Vineyards. He performed there during the winery’s summer pop-up series in July, and his regional appearances have also included venues such as Grey Sail Brewing.
Saturday therefore works as the more food-focused of the two afternoons: pizza, wine and three hours of live music without the structure or admission charge of a conventional concert.
It’s also exactly what Stonington Vineyards designed the pop-up series to be. Rather than asking visitors to plan around a major festival, the winery adds food trucks, musicians and occasional markets to an ordinary vineyard afternoon.
Sunday: Brad Bensko
Sunday shifts the musical spotlight to Brad Bensko from 2 to 5 p.m.
Bensko is one of the more established musicians working the southeastern Connecticut winery and brewery circuit, but his music reaches considerably further back than the usual acoustic-cover set.
A multi-instrumentalist, singer-songwriter, producer and recording engineer, Bensko draws heavily from 1950s and ’60s pop, the American Songbook and American roots music, combining those influences in both his original material and performances.
He has performed with blues musicians Paul Rishell and Annie Raines and with Kathleen Parks of the Boston-based group Mojo Rodeo. His own recordings lean into his interest in older sounds and recording techniques rather than simply imitating them.
That interest extends behind the mixing board. Bensko operates Bearded Cat Production, his recording studio in Mystic, and recorded his debut LP using analog reel-to-reel tape.
He’s also a particularly familiar name at Stonington Vineyards. Bensko was part of the winery’s 2026 Summer Concert Series in July and has appeared repeatedly at vineyards, farmers markets and music venues around southeastern Connecticut and Rhode Island.
Sunday’s set gives the Fall Pop-Up weekend a different character from Saturday: an afternoon built primarily around wine, the vineyard and a musician whose sound draws from several generations of American popular music.
Fall Among the Vines
The timing is part of the attraction.
By October, Stonington Vineyards looks very different from the green landscape surrounding its summer concerts. The vineyard is entering the latter part of the growing season, temperatures have cooled and fall color begins taking over the property surrounding the vines.
Stonington Vineyards has been producing wine on Taugwonk Road since the 1980s and is one of the founding members of the Connecticut Wine Trail. Its estate-grown wines have long emphasized varieties suited to the coastal New England climate, including Chardonnay and Cabernet Franc.
Visitors don’t need to attend a formal tasting to spend the afternoon at the vineyard. Wine can be purchased on site, and the Fall Pop-Ups are designed around dropping in, finding a place to relax and staying as long as the afternoon warrants.
This weekend provides two chances to do it: Brandon Donahue and wood-fired pizza on Saturday, then Brad Bensko on Sunday.
No tickets are required.
More information is available at the Event Website link below.
Details
Event: Fall Pop-Ups at Stonington Vineyards
Dates: Saturday and Sunday, Oct. 10–11, 2026
Venue: Stonington Vineyards
Address: 523 Taugwonk Road, Stonington, CT 06378
Admission: Free; no tickets required
Saturday, Oct. 10
Live Music: Brandon Donahue
Music: 2–5 p.m.
Food: G Pa’s Fired Pizza
Sunday, Oct. 11
Live Music: Brad Bensko
Music: 2–5 p.m.
Wine: Available for purchase from Stonington Vineyards
Outside Alcohol: Not permitted
Phone: 860-535-1222
Featured image is an artistic representation inspired by the event and may not depict the actual people, location, or activities shown.