Chester & Grafton Area of Vermont
The Area: Although only a few miles apart, Chester and Grafton are distantly different. Chester displays strong Victorian characteristics, while Grafton has a colonial and federal look. One is more populated and connected to neighboring communities…the other an oasis seemingly in the middle of nowhere. However, both offer the visitor unique experiences, and are equally close to activities and points of interest. Below you will find the more specific differences. Click On Photos For Larger Images
Grafton (Pop. 602): The pristine village of Grafton is like no other in Vermont. And, for good reason. For all intents and purposes, the entire village is a historic restoration. However, Grafton should not be thought of as an attraction, but rather a great place to stay or visit, for it is truly beautiful regardless of the season. And although very small, offers a degree of quality and sophistication seldom found in a rural community.
The centerpiece of the village is still The Old Tavern at Grafton, opened for business in 1801. Over the years it has accommodated the likes of Ralph Waldo Emerson, Oliver Wendell Homes, Rudyard Kipling, Daniel Webster, and Ulysses S. Grant, to name but a few. Today, along with a number of elegant B&B's located within the village, it still caters exclusively to the visitor.
Prior to the Civil War, Grafton was probably best known for its enormous sheep population and its wool. Soapstone from local quarries was also a major product of the town. However, soon after that tragic war Grafton became best known, as it is today, for its beauty and hospitality.
To do? Except for visiting some very interesting exhibits maintained by The Grafton Historical Society and The Windham Foundation, and browsing its few shops and galleries, there is little to do within the confines of Grafton other than to take some very pretty walks. However, Grafton's location is such that you are within a very short drive from almost anything you might choose to do, be it a round of golf, canoeing, or an evening of summer theater.
In winter, you’ll certainly want to spend some time at Grafton Ponds, an excellent cross-country touring center, which also offers ice skating and snowshoeing (including rentals). Grafton itself is very much a paradise for cross-country skiers, and is also not far from several downhill ski areas.
The village is also known to host some interesting events such as performances by the over 100 year-old Grafton Coronet Band, and a magnificent Fourth of July Weekend Celebration featuring the Vermont Symphony Orchestra. Check out our Calendar of Events for events such as these, and on a regular basis for exact dates and times.
Houghtonville: This is a village in Grafton known only to those residing there, and few others.
Chester (Pop. 2832): Although its "Gingerbread Victorians" command you to stop and check out the village when passing through, Chester is much more than just another pretty place in Southern Vermont. And unlike many villages in Vermont, it serves the visitor and year-round resident alike. For here you can buy a teddy bear or a text book, dine by candlelight in a lavishly appointed inn, or set yourself at the counter in either of two Diners. These, of course, are but examples of the diversity one will find in Chester. There are some very interesting shops and galleries here to explore, including some of the less obvious ones.
In addition to Chester having an interesting variety of shops and eateries, it has equally varied lodging establishments...ranging from a large full-service inn to a range of vastly different B&B's.
When in town make sure to visit Chester Depot, a place seemingly untouched by time even though it is not a preservation, just another part of town. You’ll know you’re there when you approach the railroad tracks and its truly Victorian train station. These tracks still carry freight and "The Green Mountain Flyer", an excursion train with turn-of-the-century cars, which operates regularly July thru Labor Day, and during peak visitation periods. And, if you really want to step back in time, make certain to also check out the hardware store across the street…that’s right, the hardware store!
You may also want to check out what is commonly referred to as Chester’s Stone House Village. These pre-Civil War stone houses were built with locally quarried stone and have an interesting history.
Chester is a convenient home base for those visiting Southern Vermont as it is located at the junction of Routes 11 & 103, about 20 minutes from the Interstate on Vermont's eastern boundary, and yet only about 45 minutes from Manchester and its renowned outlet stores located in the western part of the state. Equally important, it's only minutes from the tiny picturebook villages of Grafton and Weston, and from Okemo Mountain Ski Area in neighboring Ludlow.
In short, Chester is a great place to visit whether you plan to spend some time in the region, or are looking for an interesting day trip!
Chester Depot & Gassetts: These are small communities within the Chester Area, both of which carry Chester, Vermont 05143 postal addresses.
Andover (Pop. 373): Except for a very large and heavily wooded RV campground and an inn high upon a mountain, there is absolutely nothing here except a church, a used bookstore in a private home, a town office, and private residences mostly tucked away out-of-site. Andover is located approximately mid-way between Chester and Weston…way back when, Weston was part of it. Except for the inn and campground, Andover is really a place which is on the way to someplace else. It’s beautiful, and it’s a beautiful drive, but drive slowly (30 mph) through the center of Andover because you may not be the only car in town.
Simonsville: This is village in Andover (not exactly a metropolis). Whatever you may need to find in Simonsville other than a private home will be found on Route 11 between Londonderry and Chester. You probably won't even know you are in Simonsville when you're there.
Windham, South Windham (Pop. 251): This is a rural area located roughly between Grafton and West Townshend. As such, it doesn't have its own post office. The West Townshend Post Office handles mail delivery for this area. Consequently, you'll find places such as the Windham Hill Inn on the Brattleboro Area Site with an address of West Townshend.
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