Things to Do in Southern Vermont

Looking for things to do in Southern VT this weekend? You never have to spend long wondering what to do in southern VT. Whether you’re heading to a place labeled as one of the best small towns in America, planning a mountain adventure, or otherwise, something enjoyable to fill your time is always within reach. Take a look at a few places you won’t want to miss while in the southern region of the Green Mountain State.

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Fun Things to Do in Southern Vermont

1. Spend Some Time in Woodstock

There are so many fun things to do in our town of Woodstock! Check out the Billings Farm & Museum and experience rural Vermont’s past as you explore this fully-operating dairy farm. It showcases Vermont’s rural heritage and has a museum with interactive exhibits. Later you can walk around the historic Woodstock Village, exploring its boutique shops, art galleries, and eateries. The Marsh-Billings-Rockefeller National Historical Park is also worth a stop. Discover the history of conservation as you explore the forests, mansion, and gardens. While you’re here make sure to stop at Middle Bridge to see one of Vermont’s iconic covered bridges.

2. Explore Mount Ascutney in Windsor, VT

Mount Ascutney is one of the larger peaks in Southern VT at over 3,100 feet. And, because of its location, the trails to get to the summit are not always as busy as some of the other mountain exploration trails in VT. Nevertheless, it is common to have several hikers making the trek during certain points of the year. When you make it to the top via one of the four trails, you get panoramic views from the observation tower that are nothing short of awe-inspiring. Mt. Ascutney State Park surrounds the base of the mountain. Here, you can find camping, picnic pavilions, and more to explore.

3. Visit the Southern Vermont Arts Center

The Southern Vermont Arts Center is located in Manchester, VT, and is a place you don’t want to miss if you appreciate fine art. A visit to the center is one of the best ways to kill some time if you’re looking for things to do in Southern VT when it rains. You’ll see artwork from both local and international artists, and most artworks on display are actually for sale. An on-site cafe serves a mix of artisanal sandwiches and regional fare, and they also have a full bar available. Live entertainment is scheduled at different times throughout the year, including music showcases, operas, and more.

4. Check out the Merck Forest and Farmland Center

If you make your way to the top of Rupert Mountain, you’ll find a massive expanse of open land to explore by foot, on horseback, or even cross-country skiing in the winter. The Merck Forest and Farmland Center is open every day all year and provides visitors with over 30 miles of trails to travel. You can go on guided hikes, take part in educational workshops, or even just book a stay in one of the quaint on-site cabins to enjoy the natural surroundings overnight.

5. Go thrifting and antiquing in Manchester

Manchester in Southwest VT is an interesting place where people from many cultures and tastes collide. With that being said, it can be a lot of fun to explore thrift shops, antique stores, and consignment stores in the area. You’ll find places like Finial & Parquet and The Vintage Soul on Main Street if you love antiques. The Zippy Chicks consignment store is nearby, as well as Perfectpiece, which boasts 5,000 square feet of everything you can imagine for the home from rugs to artwork.

6. Check out one of the best small towns in America: Brattleboro

Brattleboro, VT is nestled just east of the Green Mountain National Forest. This charming small town has made a lot of lists, including being named one of the “Best Small Towns in America” by the Smithsonian. Brattleboro has just as much to offer as bigger nearby cities, including museums like the Brattleboro Museum & Arts Center, tons of shopping opportunities, great food, and fascinating historical sites. If you happen to visit in the winter, the Brattleboro Winter Carnival happens every year and involves everything from ice skating to sleigh rides.

Hungry? Check Out These Top VT Eateries

After exploring all the best things to do in Southern VT, you may have a healthy appetite. Good food is always just around the bend. A few local treasures for good food include:

• Chelsea Royal Diner in Brattleboro
• Green Mountain Sugar House in Ludlow
• Arlington Dairy Bar in Arlington
• Fireworks Italian in Brattleboro
• La Casita in Wilmington

Swing By Sunday Drive for High-Quality Cannabis

If you’re in the Southern VT region, we hope to see you at Sunday Drive in Woodstock. We strive to keep the spirit of the state alive in everything we do, right down to the appearance of our cannabis store. Our recreational dispensary highlights only the most trusted cannabis brands in the state. Also, you can visit our menu online before you arrive, and we’ll have your order ready for pickup during business hours.

Shop Cannabis in Southern Vermont