Grey Sail Oktoberfest Brings German Music, Steinholding and a Bavarian Menu to Westerly
Grey Sail Oktoberfest Brings German Music, Steinholding and a Bavarian Menu to Westerly on Sunday, Oct. 11, turning the brewery’s Canal Street beer garden into a six-hour celebration with German music, seasonal beer, bratwurst, pretzels, wood-fired pizza and a qualifying round of a national steinholding competition.
The party runs from noon to 6 p.m. at the Grey Sail Taproom, with the brewery leaning further into the German festival tradition than simply putting an Oktoberfest beer on tap. The Vagabonds provide the soundtrack, Vetrano’s Wood Fired serves a special Bavarian-inspired menu and guests can try both steinholding and yodeling competitions.
For Grey Sail, there’s also some history behind this particular Oktoberfest. The brewery is approaching its 15th anniversary, while the German band playing the festival is preparing to call it quits after 40 years.
The Vagabonds Bring 40 Years of German Music to the Beer Garden
The music comes from The Vagabonds, a New England German band formed in 1986 specifically to preserve and perform German-American music.
This appearance carries more weight than a typical Oktoberfest booking. The Vagabonds have announced that 2026 will be their final season, ending a 40-year run.
Their farewell schedule is filled appropriately with Oktoberfests and German-American celebrations around New England, including appearances in Connecticut, Massachusetts and Rhode Island. The band specifically describes its Grey Sail stop as an outdoor beer garden event.
That should give Grey Sail’s Oktoberfest something close to the atmosphere the event calls for: German festival music played live in a brewery courtyard rather than a generic cover band added to a beer festival.
The Beer Is Built for October
Grey Sail is bringing out two of its fall beers for the occasion.
Autumn Winds Fest Bier is Grey Sail’s take on an Oktoberfest-style lager, built around a malt-forward profile with toasted flavors, a touch of sweetness and a clean finish.
The considerably more Halloween-minded alternative is Headless Oarsman Pumpkin Ale, a 6.5% ABV seasonal inspired by the legend of Sleepy Hollow. Grey Sail brews it with pumpkin spice purée, producing cinnamon and clove notes over a rich malt base.
Fall-inspired cocktails will also be available.
Guests who want to go all-in can purchase Grey Sail steins and use them throughout the day.
Vetrano’s Gives Its Wood-Fired Menu a Bavarian Detour
The food side gets its own Oktoberfest treatment.
Vetrano’s Wood Fired, which operates its pizza shed at Grey Sail, is serving a special menu built around bratwurst, pretzels and an Oktoberfest pizza.
The Bavarian Bratwurst is grilled and served with sauerkraut and a choice of spicy brown or yellow mustard.
Headless Oarsman Pretzel Bites pair warm pretzels with a beer-cheese sauce made around Grey Sail’s pumpkin ale.
Then there’s the Beer Hall Brat Pizza, a wood-fired pie topped with bratwurst, beer cheese, mozzarella, caramelized onions, crispy onions and spicy brown mustard.
It’s a substantial departure from Vetrano’s regular pizza menu, which normally ranges from Margherita and pepperoni to Calabrese, Diavola and other wood-fired specialty pies.
Oct. 11 also has another significance for Vetrano’s: Grey Sail currently lists it as the final day of the pizza shed’s 2026 season at the brewery.
Hold a Stein. Go to the Regional Championship.
At 4 p.m., the afternoon becomes competitive.
Grey Sail is an official U.S. Steinholding Competition qualifier venue this year. Competitors attempt the deceptively simple Bavarian endurance challenge: hold a filled beer stein straight out in front of the body for as long as possible without lowering or improperly supporting the arm.
The Grey Sail winner receives a stein and advances to the regional championship.
Steinholding, or Masskrugstemmen, has become one of the most recognizable American Oktoberfest competitions. What initially looks like a test of arm strength quickly becomes one of endurance as competitors try to keep a heavy filled stein extended horizontally.
There will also be a yodeling competition, with another Grey Sail stein going to the winner.
Oktoberfest Inside a Former Macaroni Factory
Even Grey Sail’s home has a food-and-grain connection stretching back nearly a century.
The brick building at 63 Canal Street was constructed near the end of the 1920s as the Westerly Macaroni Factory. It later housed a U.S. Postal Service parcel operation and NAPA Auto Parts before Jennifer and Alan Brinton acquired it for their brewery.
Grey Sail moved into the building on April 4, 2011. After seven months of renovations, its first batch of Flagship Ale was brewed on 11/11/11.
Fifteen years later, the brewery has expanded beyond that original brick building. The neighboring Taproom at 65 Canal Street provides indoor seating and the outdoor courtyard that has become a warm-weather gathering place for live music, food and community events.
Grey Sail will celebrate its 15th anniversary later in October, making Oktoberfest part of a particularly busy month at the brewery.
On Oct. 11, though, the formula is much more German: Fest Bier in a stein, bratwurst and pretzels from the wood-fired kitchen, a veteran German band playing its final season and, for anyone with enough shoulder endurance, a chance to advance in competitive steinholding.
More information is available at the Event Website link below.
Details
Event: Grey Sail Oktoberfest
Date: Sunday, Oct. 11, 2026
Time: Noon–6 p.m.
Location: Grey Sail Taproom
Address: 65 Canal Street, Westerly, RI 02891
Music: The Vagabonds German Band
Featured Beer: Autumn Winds Fest Bier and Headless Oarsman Pumpkin Ale
Other Drinks: Fall-inspired cocktails and additional Grey Sail offerings
Food: Vetrano’s Wood Fired Oktoberfest menu
Bavarian Bratwurst: Grilled bratwurst with sauerkraut and spicy brown or yellow mustard
Headless Oarsman Pretzel Bites: Warm pretzels with Headless Oarsman beer cheese
Beer Hall Brat Pizza: Bratwurst, beer cheese, mozzarella, caramelized onions, crispy onions and spicy brown mustard
Steinholding Competition: 4 p.m.; U.S. Steinholding Competition qualifier
Steinholding Prize: Grey Sail stein and advancement to the regional championship
Yodeling Competition: Winner receives a Grey Sail stein
Steins: Grey Sail steins available for purchase
Family Friendly: Yes
Dogs: Leashed dogs permitted in the outdoor Taproom courtyard
Parking: Brewery and Taproom lots plus satellite parking at 75 Canal St. and 39 Canal St.; municipal parking is available at 14 Canal St. near the Westerly train station
Taproom Phone: 401-596-4151
Featured image is an artistic representation inspired by the event and may not depict the actual people, location, or activities shown.