The lively town of Bennington, Vermont, springs to life in May, marking the start of the outdoor festive season. With trees in full bloom and downtown’s historic streets adorned with vibrant flowers, this is the perfect time to explore all that Bennington has to offer. From festivals and live music to outdoor dining and scenic views, we’ve got you covered with a guide to the must-see events and destinations in May!

Bennington in Bloom

Downtown Bennington comes alive with a vibrant mix of hydrangeas, dahlias, verbena, and petunias, all freshly planted for Memorial Day weekend. Photo provided by Bennington Banner.

Memorial Day weekend in Bennington marks the start of a vibrant and colorful season. The streets come alive with foot traffic as locals and visitors enjoy the lush flower displays and newly opened outdoor spaces. Popular attractions like the Bennington Museum, Park-McCullough Historic Governor’s Mansion, and the Robert Frost House Museum welcome guests, while the warming weather invites hikers to explore the trails. Nearby, Lake Paran and Lake Shaftsbury gear up for summer activities. Whether you want to hike, visit historic sites, or just enjoy the lively atmosphere, Bennington, Vermont, is a fantastic destination in May.

Outdoor Dining

Outdoor dining is back in swing at the Mt. Anthony Country Club’s restaurant, The Grill, in Bennington. Beer on tap and their lobster roll are popular orders. Vermont Country Magazine photo.

In May, Bennington’s dining destinations and craft breweries set the stage for outdoor enjoyment. Experience riverside dining at Pangaea Lounge in North Bennington and Miller’s Toll Outdoor Deck in Bennington, or enjoy casual outdoor seating at Kevin’s, Dutchman’s Tavern, Ramunto’s, Harvest Brewing, Philly’s, or the patios at 421 Craftbar and Kitchen, and Union South. For stunning views, head to the Mount Anthony Country Club, perfect for a relaxing drink or meal, or try the deck at Publyk House for another great vantage point. View Bennington’s complete dining directory here.

Outdoor Festivals and Events

Hundreds of people came out for the Southern Vermont Summer Homebrew Festival in 2023. Photo provided by Southwestern Vermont Chamber of Commerce.

Southern Vermont HomeBrew Festival (May 4, 2024)

Get ready for the 14th Annual Southern Vermont HomeBrew Festival on May 4! This year’s event promises over 100 different beverages to sample, a street festival vibe, food trucks, live music, and vendors. The “May the 4th Be with You” theme brings Star Wars costumes, themed beers, and film screenings throughout the day. Don’t miss this exciting blend of great drinks, delicious food, and Star Wars-themed fun!

Hemmings Cruise-Ins and Thursday Night Live (Starting May 16, 2024)

Photos provided by Better Bennington Corporation.

Starting May 16 and continuing every third Thursday through August, the Better Bennington Corporation (BBC) hosts Hemmings Cruise-Ins (5-8 pm) alongside Thursday Night Live performances at the Thomson Stage in Merchants Park (6-8 pm). This combo of classic cars and live music makes downtown Bennington the place to be on those Thursdays. It’s a fantastic opportunity to mingle with the community and enjoy the festivities.

37th Annual MayFest (May 25th, 2024)

Though rain had been predicted, Mayfest drew large crowds to downtown Bennington. Photo by Michael Albans – Bennington Banner.

Bennington’s annual arts and crafts festival, MayFest, is back on May 25th from 10 am to 5 pm, with over 70 vendors, live music throughout the day, and specials and discounts at participating downtown businesses. This family-friendly event is free to the public and offers something for everyone. Check out the latest updates and music line-up on the Better Bennington website and follow them on social media @DowntownBennington on Facebook and Instagram for all the latest news.

Experience Bennington This May

Photos provided by the Bennington Banner.

May is an ideal time to explore Bennington, with its lively events, beautiful scenery, and welcoming community. Whether you’re a local or visiting for the first time, there’s no shortage of things to do and see. So, grab your friends and family and join us for a fantastic start to the outdoor festive season.

For more information on upcoming events, attractions, and places to eat, visit our website and follow us on social media.

We can’t wait to see you in Bennington!