Arts, Dining & Entertainment

Find a wide variety of events from across Rutland and Windsor Counties that are open to the public; from art gallery openings to library events to theater performances to sheep sheering events and everything in between! (For live music events see the music scene category.) Got an event coming up that we should include? Please let us know! Email [email protected]

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Courtesy Billings Farm Visitors will get up and personal with some woolly friends during Billings Farm’s Sheep & Wool Day on May 24.

Billings Farm to host Sheep & Wool Day

May 21, 2025
Saturday, May 24 from 10 a.m.-5 p.m.—WOODSTOCK — Billings Farm & Museum will celebrate Vermont’s long-standing sheep farming tradition on Saturday, with its annual family Sheep & Wool Day. This hands-on event highlights the journey of wool from fleece to fiber. This family-friendly event invites visitors of all ages to explore the rich history and…

Sip & Shop is back in Downtown Rutland

May 21, 2025
Downtown Rutland Partnership’s popular Spring Sip &  Shop pairs local beverage and food producers with downtown Rutland businesses. Ticket holders will visit up to 20 stops where they can shop, enjoy sales and raffles, taste something new, meet up with friends and enjoy an evening downtown together. Tickets are on sale at downtownrutland.com/sipandshop.  Ticket options…

Local students win statewide tree-themed art and essay contest

May 21, 2025
WHITE RIVER JUNCTION,  MENDON — Two area students were among this year’s winners in the Growing Works of Art contest, a statewide program encouraging Vermont students to explore their connection to trees through art and writing. The 2025 theme, “Tree Tales from A to Z,” invited students in grades K–8 to select a letter of…

Killington Resort rolls out full slate of summer events and adventures for 2025

May 21, 2025
KILLINGTON — The snow may be gone, but the action is just heating up at Killington Resort as it unveils a packed summer schedule for 2025. From mountain biking and music to races and family fun, “The Beast” delivers non-stop excitement across its expansive terrain, with new additions and returning favorites lined up throughout the…

From Slopes to Service: KMS seniors host fundraiser at The Foundry

May 21, 2025
By James Kent Thursday, May 29 at 4 p.m.—KILLINGTON — The senior class of Killington Mountain School (KMS) will trade their ski gear for menus as they take over The Foundry at Summit Pond for a special fundraising event. In a unique partnership between KMS and the Karr Group, the evening will feature the 2025…

Discover More from This Category: Arts, Dining & Entertainment

Billings Farm to host Sheep & Wool Day

May 21, 2025
Saturday, May 24 from 10 a.m.-5 p.m.—WOODSTOCK — Billings Farm & Museum will celebrate Vermont’s long-standing sheep farming tradition on Saturday, with its annual family Sheep & Wool Day. This hands-on event highlights the journey of wool from fleece to fiber. This family-friendly event invites visitors of all ages to explore the rich history and…

Soderbergh’s ‘Presence’ features more than scares

May 21, 2025
‘Presence’ is available to stream on-demand After director Steven Soderbergh’s planned 2013 theatrical film, “Behind the Candelabra,” ran into funding difficulties and eventually landed on HBO for a cable release, the prolific director announced his retirement. In what is, perhaps, the shortest retirement in filmmaking history, Soderbergh was back with his short-lived, though compelling, two-season…

Inside Vermont’s creative heart: Artists open their doors for an inspiring Spring Open Studio Weekend

May 21, 2025
May 24-25—VARIOUS LOCATIONS—Throughout Vermont, artists are preparing to welcome the public into their creative spaces for the annual Spring Open Studio Weekend. This statewide event invites visitors to explore studios, galleries, and art centers on scenic drives through town centers and rural backroads alike. The event, organized by the Vermont Crafts Council, runs from 10…

Cobra gymnasts completes 13th year of competitions in Vermont

May 21, 2025
By Shelby BarsalouEditor’s note: Shelby Barsalou is the owner of Cobra Gymnastics. Cobra Gymnastics of Rutland City has brought their 13th competitive season to a strong close with an impressive showing at the USA Gymnastics Region 6 Championships in Westford, Massachusetts on May 17-18.  During the Vermont State Championships on March 22-23, 409 athletes from…

On your marks, get set, bow!

May 21, 2025
Total Archery Challenge returns to Pico for three days of competition May 23 through 25—KILLINGTON — Archers, outdoor enthusiasts, and families will gather at Pico Mountain Resort for a one-of-a-kind event this Memorial Day weekend as the Jack Link's Total Archery Challenge returns for three days of world-class 3D archery action, Friday through Sunday. Billed…

Listings May 21-27

May 21, 2025
WED 5/21 LUDLOW6 p.m. Off the Rails – Learn to Line Dance POULTNEY7 p.m. Poultney Pub – Open Mic hosted by Danny Lang QUECHEE6 p.m. The Public House – Chris Pallutto RUTLAND8 p.m. Center Street Alley – Full PA/Backline Open Mic hosted by Josh LaFave THUR 5/22 BRANDON5:30 p.m. Red Clover Ale Company – Open…

Lawson’s Finest Wins Silver at World Beer Cup for Vermont-Brewed Fayston Maple Imperial Stout

May 14, 2025
WAITSFIELD — Lawson’s Finest Liquids earned international recognition earlier this month, winning Vermont’s only medal at the 2025 World Beer Cup, the world’s premier professional beer and cider competition. The brewery’s Fayston Maple Imperial Stout claimed a silver medal in the British-Style Imperial Stout category, celebrated for its robust flavor and strong Vermont roots. The…

Bookstock in Woodstock: A Literary Play on Words

May 14, 2025
WOODSTOCK—This year Woodstock’s Village Green will again come alive with stories, music, and local spirit as Bookstock returns May 16 through 18. This popular three-day festival welcomes book lovers, poets, and curious minds for a vibrant weekend of author talks, poetry readings, hands-on workshops, music, children’s activities, food vendors, and more. Events kick off Friday…

‘Nonnas’ is a ‘cheesy,’ slice of goodness

May 14, 2025
By Ellie Trinkle It has long been suggested that the power of food transcends beyond simply “tasting good”; it can heal, invite, and inspire. Stephen Chbosky’s new Netflix film “Nonnas” depicts this multitude of food in a heartwarming and tender way. The film follows middle-aged Joe Scaravella, played by Vince Vaughn, whose mother’s recent tragic…

Vermont Symphony Orchestra unveils bold and diverse 2025–2026 Season

May 14, 2025
The Vermont Symphony Orchestra (VSO) has announced an ambitious and wide-ranging 2025–2026 season that blends audience favorites with adventurous new programming, highlighting the orchestra’s ongoing commitment to artistic excellence, community engagement, and musical innovation. Marking its 91st year, the VSO will offer a season packed with musical treasures—from holiday traditions to contemporary premieres. Season highlights…

Little Feat rocks Rutland with new tunes and classic hits

May 14, 2025
The Little Feat show at the Paramount Theatre on Cinco de Mayo was a 10. This performance was the kick-off of their “Strike Up The Band” tour, supporting their just-released album of the same name. This is Little Feat’s first album of new original songs in 13 years.  “Tonight was rockin’ ,” said Little Feat’s…

Listings May 14 – May 20

May 14, 2025
WED 5/14 LUDLOW6 p.m. Off the Rails – Learn to Line Dance POULTNEY7 p.m. Poultney Pub – Open Mic hosted by Danny Lang QUECHEE6 p.m. The Public House – Kim Wilcox RUTLAND8 p.m. Center Street Alley – Full PA/Backline Open Mic hosted by Josh LaFave WOODSTOCK5:30 p.m. Town Hall - Zack’s Place Presents: Z Lion…

Dozens turn out for 4th annual Peavine Whitewater Race despite rain

May 7, 2025
By Mike McDonnell Whitewater enthusiasts from all over Vermont and at least six other states converged on the White River in Stockbridge Saturday, May 3, to compete in the 4th annual Peavine Whitewater Race. In total, 52 racers disregarded the sporadic rain showers as they navigated the five miles of rapids between Ted Green Ford and…

‘Secret Mall Apartment’ takes street art to a new level

May 7, 2025
Director Jeremy Workman’s documentary, “Secret Mall Apartment,” spins a crazy yarn about a group of Rhode Island street artists who, in a brazen and ingenious-level piece of establishment corporate defiance, fooled the Providence Place security for four years by building a secret apartment within a hidden nook of the mall structure. Artist Michael Townsend is…

Steak on a bun: The Hangry Hogg smash burger is a local legend in the making

May 7, 2025
By James Kent If you’ve driven past the corner of West Street and Main in Rutland around lunchtime in the past few months, chances are you’ve recognized the food truck with the big pig chef logo on the side and large letters spelling out "Hangry Hogg" with the tagline, “Put some South in your mouth.”…