Explore These 5 Underrated Southern Vermont Towns: (and things to do in each)

Amanda Clark-Rudolph

Check out these BEAUTIFUL 5 underrated Southern Vermont towns that offer something for everyone.


Photo by Cameron Venti on Unsplash

You've got to remember, Vermont is a lot of beautiful mountains with valleys and small brooks that run into bigger rivers. - Pete Shumlin

Known for the Green Mountain Boys, Maple syrup, and extraordinary foliage, Vermont is a sweet destination many don't know much about. Visitors tend to gravitate to the well-known Burlington area, but miss out on the rural, small-town charm in underrated southern Vermont towns.

That's why I'm sharing insights on small Vermont towns that you may have never heard of but have so much to offer.

I moved from Vermont to Florida for the weather and to be near family, so I know firsthand about some sweet underrated southern Vermont towns that are gems along the beaten path.

Conveniently, these beautiful destinations are also all within an hour or two of each other, so you could easily hit them all while traveling through the Green Mountain State.

Note: Due to the pandemic, please double check on the hours below. They may have changed since this was written.

So, without further ado, here are a few underrated southern Vermont towns that you won't want to miss.

1. Londonderry

Okay, I’m a little biased here, because Londonderry was my hometown growing up, and I could write a full article, or book for that matter, on this quaint, rural, yet spectacular destination.

Even though Londonderry doesn't sport any malls, tall buildings, or stoplights, it epitomizes that small-town charm you won't want to miss.

While there, take a kayak out for a spin at Lowell Lake for a secluded and peaceful afternoon where you can fish and paddle.

And, after working up some hunger, catch a bite in town at the laid-back Garden Market, which has gourmet sandwiches like the Smokin' Tempeh and Turkey Reuben.

For an added treat, if you've ever heard of Burton snowboards, they made the very first one right across the street.

Keep heading through town, and you'll reach Pingree Park, which hosts summer concerts, and features a playground, dog park, basketball courts, baseball fields, tennis courts, and a nature trail.

It's a perfect place for a picnic under the pavilion, too.

Things to know

  • Lowell Lake - Best to visit May through October, open 10 am to sunset.
  • The Garden Market - open daily 10 am-6 pm
  • Pingree Park open year-round, 24 hours

2. Weston

If you're a theater fan, you won't want to miss a summer show at the Weston Playhouse. This 83 year running theater by the river has showcased actors like Christoper Lloyd, Christopher Reeves, and more.

I've never seen a bad show there, but a few that stick out from the past are Gypsy, Hairspray, and Fiddler on the Roof.

Before or after the show, check out the Vermont Country Store, which sells old-fashioned candy in jars, cow slippers, homemade soap, and an assortment of other Vermont-based products.

On your way out, swing by the sample section where you can score free jam, mustard, or honey on oyster crackers.

Outside you can eat a full meal at Mildred's Dairy Bar, while you sit on a wooden swing table and chow down on some maple ice cream and burgers.

And after, hit the Christmas shop and art galleries that are all within walking distance from the store.

Things to know

  • Weston Playhouse open June-October, experience a matinee or evening performance
  • The Vermont Country Store open year-round, 11 am-3:30 pm
  • Mildred's Dairy Bar Open during the summer, 10 am-6 pm.

3. Stratton

No matter which season you visit, Stratton Village presents a unique and breathtaking landscape at a 3,199' elevation.

With pub food from Mulligans, feel-good coffee shops like Coyote, and a variety of stores (including the Mountain Sweets Candy and Toys), this small ski town of Stratton is a hit during any time of the year.

Whether you're there to ski the slopes, golf, ride the gondola, or hike up the mountain, you'll have no shortage of things to do at this southern Vermont destination.

Things to know

  • Mulligans open year-round, 11 am-10 pm
  • Stratton Village shops, open year-round, hours vary
  • Stratton Mountain Golf - Projected season start date: May, open 7:20 am-6 pm,
  • Gondola - July - days and times vary.

4. Manchester

Eager to swim in a gorgeous pond that reflects the clear Vermont skies and birch trees? Then visit the Equinox Pond in Manchester, VT, where you might run into a few fly fishermen, too.

After, venture to Orvis, where you can attend a fly fishing school or stock up on outerwear.

In downtown Manchester, there are many sweet shops and restaurants, like Zoeys, which makes the best homemade potato chips ever!

While in Manchester, you'd want to check out Hildene, the estate of Lincoln's son, Robert Todd Lincoln, and the Southern Vermont Arts Center that rocks massive steel sculptures on your drive up to the galleries.

This naturesque town also offers the opportunity to rough it in the woods for a short or long hike by hopping on the Appalachian Trail that's only 5 miles from the town's center.

Things to know

  • Orvis - Open year-round, 10 am-6 pm
  • Zoey's Double Hex, open year-round, 11 am-9 pm
  • Hildene - open year-round, 9:30 am-4:30 pm
  • Southern Vermont Art Center, open year-round 11 am-5 pm (Sundays 12-5 pm)

5. Brattleboro

Seeking arts and culture, downtown cafes, and unique shops? Brattleboro is it. Situated in the striking Windham county, Brattleboro is a southern Vermont town you won't want to miss.

While there, visit the Brattleboro Museum of Art and Culture. Founded in 1972 and residing in the former Union Station, this museum showcases both local and international artists and also acts as a community center.

Take note that there’s also a music and a historical center nearby. In Brattleboro, you’ll also find a kids' space, enticing hiking trails, and farmers' markets. You won't regret a visit to this underrated Vermont town.

Things to know

  • Brattleboro Museum of Art and Culture, open Wednesday through Sunday 10 am-4 pm
  • Brattleboro Music Center, Currently not scheduling in-person events, visit the center's website for virtual experiences.
  • Brattleboro Historical Society, Open Thursday - Saturday 2-4 pm, Saturday 10 am-noon.

Wrapping Up

So, if you've been planning on getting up north and seeking some out-of-the-box memorable destinations, visit these 5 southern Vermont towns and don't forget to bring me back some award-winning maple syrup!

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Hi, I'm Amanda - a freelancing mama who writes about family, travel, holidays, and more! In addition to freelancing it up, I'm a Content Coordinator for neighborhood magazines. My favorite pastimes: Writing, slurping lattes, and playing freeze tag with my two sons.

Ocala, FL

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