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Covered Bridge Woodstock VT

No, I’m not referring to Shiretown in the Hobbit. It’s somewhere nearly as magical though. Woodstock is the County Seat for Windsor County VT, making it the Shire Town for that county, hence the nickname that you will see sprinkled throughout the village.

Woodstock Vermont would probably surprise most newcomers. It is a very culturally connected community, while maintaining a quaint Vermont village ambiance. There’s a rural charm that seems to bring us back to ‘the good old days’ there. It hasn’t changed much visually in the last 100 years or more, luckily for us travel adventurers.

Houses Bordering Woodstock Village Green

Storybook Woodstock Village Green and surrounding homes and municipal buildings seem to have emerged straight from the 1800s. Granite, Marble and immaculately trimmed wooden buildings of a bygone era circle the green like a necklace. There is so much history  encompassed within the proximity of this circle. Art galleries, libraries, stately homes, a bank, a courthouse, and Town Hall are some of the interesting sites to be found bordering The Green.

The Historic Woodstock Inn, originally built in 1792 and rebuilt in 1969, sets back off The Green, rising majestically. An 18-hole golf course associated with the inn is just a couple of minutes drive on a scenic back road, beyond the village. An inviting covered bridge leads from The Green and crosses the Ottaquechee River to the other side of town.

Art Gallery in an Old Home on The Green

The Village Green is actually a beautiful and immaculately kept park, complete with vintage park benches, historic markers and a very comprehensive information booth, in season. This hub in Woodstock has been a favorite picnic destination of mine for decades. My children and I would make a quest of filling a picnic basket on the journey from home to Woodstock. We’d stop at farm stands, bakeries and country stores along the way and add a loaf of fresh bread, Vermont cheddar cheese, local cider and honey, crisp apples and anything else that was produced nearby and was seasonal. We’d arrive at the Village Green and spread a blanket or commandeer a park bench to enjoy our Vermont feast while watching the world go by all around us.

Shire Apothecary in Woodstock

The village itself was settled in 1768. Woodstock owes much of its current architecture and character, to being a resort community since the late 1800s when the railway brought tourists from Boston and New York City.

Woodstock Shops

Woodstock also owes much, especially in the way of its preservation, to the influence of the Marsh, Billings and Rockefeller families, who moved to the area several generations ago and have been enormous benefactors to the region ever since. Those generous former residents have made some significant contributions like the Marsh-Billings-Rockefeller National Historical Park and the Billings Farm & Museum that will preserve ways of life and property in Woodstock for all posterity. These sites are located just a few minutes walk from the Village Green, across either of two convenient bridges and the picturesque Ottaquechee River.

Downtown Corner in Woodstock

Woodstock is very walkable. It is laid out conveniently and all the commerce is located within a couple of blocks. Immediately adjacent the green, are a few old-fashioned downtown streets, with a continued sense of perfect old-time New England about them. Interesting vintage architecture lines the streets, many buildings made of local stone, seemingly rooted to their foundations. Many businesses have been in operation for decades, including Gillingham’s Country Store, a landmark in this community.

Justin Morgan Sign on The Green

There are a variety of other interesting little shops tucked in along these streets. Quaint bookshops, a kitchen equipment store, toy and handmade jewelry shops, a vintage clothing shop, a butcher shop and deli and a Victorian boutique, and the Woodstock Historical Society, just to name a few.

Woodstock Home on a Side Street

Beyond the immediate center village area, well-maintained roads and streets house sleepy neighborhoods with lovely old Vermont homes, many boasting welcoming-looking front porches and garden; a bit of quintessential small town America. Beyond town there are camping areas, horse farms, and other inviting locations, in adjoining communities like Bridgewater, Barnard and Quechee.

Lovely Woodstock Front Porch

After many years of taking day trips to Woodstock several times each year, I was finally able to attain a wish from my ‘old inns’ wish list. Last summer we stayed overnight in Woodstock at the Woodstock Inn and I was able to walk for miles in and around the village without keeping track of the time to allow for the ride home. Truly a dream come true!

For a taste of ideal New England rural village life, I highly recommend visiting Shiretown soon. There’s something for everyone here and Woodstock really shines in every season.