Chester, Vermont

Chester Town office: 802-875-2173

Population: 3044

Sq. miles: 55.9

Chester, Vermont Links:

Click here to view the Chester, Vermont Business Directory

10 Safest Cities in Vermont

Chester, Vermont is what one thinks of when it thinks of the “quintessential Vermont town;” quaint, charming, and brimming with life. Nestled between Bromley, Magic, Stratton, and Okemo Mountain, Chester, Vermont is the southern gateway to the Okemo Valley. Chester is chock full of architectural treasures, vibrant personality, unspoiled countryside and unrivaled hospitality.

One of the Prettiest Places in America!

Nominated as one of the prettiest “Painted Places” in America, Chester, Vermont’s exquisite village green welcomes you to explore the town’s many superb restaurants and taverns, shops and eclectic galleries.

Chester’s rich history and profound sense of purpose have preserved its timeless quality and peaceful character. Chester, Vermont has fostered towering maples, championed contemporary arts, and flourished with family farms. Home to The Stone Hearth Inn & Tavern named one of only ten “Green Restaurants in the Green Mountain State” by the Vermont Business Environmental Partnership, Chester abounds with delightful inns and award-winning B&Bs like the Inn Victoria, lively arts and culture, stunning scenery and peerless tranquility for anyone looking to ‘get away from it all,’ even if just for a little while.

Interested in walking through Chester?  Here’s both a map with several routes and a guide.

Take a hike!

Chester boasts much in the way of artisans, antiques and a famous “Chester Craft Fair” but did you know there’s a few prized walks and hikes you can explore too?  Check out the Lost Mine or GMUHS hikes to see the natural wonders of our area.


Chester’s 2015 Summer Concert Series returns to the Academy Building lawn across from the Green in downtown Chester with five Thursday night concerts from 6:30-8:00 pm starting July 16, 2015.

Kicking off the series on July 16th are local favorites, The Bondville Boys, with their eclectic, hard-edged bluegrass. Musicians Jake Geppert, Tom Morris and Laura Molinelli have played together for over twenty years. Now joined most recently by Ben Campbell and Christian Heins, The Bondville Boys are known for their sweet harmonies, excellent musicianship, great energy and original tunes.  New this year on July 23th are Frydaddy and the Little Town Horns. Led by Carlos Ocasio, the Frydaddy band has been rocking the Upper Valley for close to 30 years. With influences ranging from James Brown to Carlos Santana, their original tunes will make for a foot stompin’ good time.  They will be followed on the 30st of July by Andover’s own Ida Mae Specker and her band, The Honest Mistakes. Ida, a 3rd generation fiddle player, is a powerhouse on stage- she fiddles, drums, and sings simultaneously in a whirlwind of passion and virtuosity.  On August 6th, Gerry Grimo and the East Bay Jazz Ensemble return to Chester to deliver the amazing big band sounds that have captivated concert- goers in the past. With their 10-13 piece ensemble (and lots of sax) delivering the best in jazz, pop and R & B music, they will take you on a sentimental journey through the sound of the classic big bands. And to wrap up this year’s concert series, on August 13th, Chester’s own Chris Kleeman Band, Vermont’s best kept Blues secret, performs some of Chris’ own tunes and old traditional and Chicago-style Blues.

Brought to you by the Rotary Club of Chester, Vermont, The Chester Summer Music Series thanks its major patrons, Newsbank, TDBank, and Dakin & Benelli. Additional support comes from sponsors  Fullerton Inn, Chester Family Medicine/SMCS, Vail Law Office, and The Vermont Country Store. Subscribers include Chester Hardware, Lisai’s Chester Market, Skygate Financial Group, Ulbrich Law Offices, Terrigeneous Landscape Architecture and The Message for the Week (in-kind). Friends are Barrett & Valley Real Estate, Moon Dog Café, Misty Valley Books, MacLaomainn’s Scottish Pub, and Motel in the Meadow. It is thanks to the generosity of these local businesses that we are able to bring you these wonderful summer concerts. And the biggest thanks go to the Rotary Club of Chester, Vermont which has generously supported this series through the years.

Bring your blankets and lawn chairs and be prepared to sit back and listen to great music on a summer night right in downtown Chester.  In case of inclement weather, concerts will move to MacLaomainn’s Scottish Pub, 52 South Main Street, Chester.

Contact: Lynne Reed at Misty Valley Books 802 875-3400

Located just west of the junction of Routes 11 and 103 along the Middle Brook of the Williams River, Chester, Vermont offers the best of Vermont’s celebrated pristine landscape and lively community with opportunities for bicyclists, boaters, shoppers, sightseers and anyone looking for a quiet respite or intrepid recreation, and all within easy distance of the Okemo Valley region’s top winter resorts.

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