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GreaterUpperValley.com

Events Happening Labor Day Weekend

Aug 27, 2026 11:05AM ● By Elise Renaud

One of the annual long weekends for most people in the United States is coming up. If you’re looking for something fun to do this Labor Day weekend, here’s a list of some fun events to go to:


Harpoon x L.L.Bean Flannel Friday Launch Party

On Saturday, Harpoon Brewery in Windsor, VT, is launching Harpoon x L.L.Bean Flannel Friday, its limited-edition collaboration beer inspired by the traditions that make autumn in New England unforgettable.

From 3 p.m. to 7 p.m., guests can enjoy live music, enter to win LL Bean gear, enjoy complimentary s’mores and rootbeer floats, and more.

Learn more about this free event here.


New World Festival

The New World Festival in Randolph, VT, also known as “Vermont's premier Celtic & Québecois music festival,” is happening on Sunday.

“This vibrant celebration of music, dance, and culture promises to be a day filled with joy, excitement, and unforgettable memories. With a lineup featuring talented artists from around the world, you'll be treated to a diverse range of performances that will ignite your senses and leave you inspired,” the description reads.

The event features local food vendors. Learn more here.


Hopkinton State Fair

The annual Hopkinton State Fair is happening Thursday through Monday.

“Join us for an unforgettable experience filled with thrilling Midway rides, live music, delicious food, and exciting competitions like the Demolition Derby Grandstand Show,” the website said.

Learn more about the Labor Day Weekend tradition and get tickets here.



Lebanon Brew Fest

The Rotary Club in Lebanon is holding its annual Brew Fest. from noon to 4 p.m. on Saturday. The 21 and older event allows festivalgoers to “sample from over 35 renowned local beer vendors, feast on mouthwatering bites from local food trucks, and dive into games and activities that promise something for everyone.” Non drinking tickets are available. Learn more and get your tickets here.


Labor Day Weekend Craft Fair

The Labor Day Weekend Craft Fair at Gunstock Mountain Resort is happening Saturday and Sunday.

“There will be over 100 exhibitors with items for sale including hand painted glass/metal/wood/mushrooms, beautiful folk art, handcrafted inlaid wooden mirrors and tables, chainsaw wood carvings with demos by Elise, pottery, custom leather belts and beautiful totes/pocketbooks, acrylic and watercolor fine art, gourmet oils and vinegars, pressed floral art, New Hampshire maple syrup, hand poured soaps, soy candles, jewelry, quilts and quilted wall-hangings, charcuterie boards, children's chalkboard mats, macrame furniture, wildlife photography, custom signs, amazing baked goods, and lots more! Live Music with North River both days,” the event’s website said.

Learn more about this dog-friendly event here.



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