Vermont is known for many things, Mountains, Farms, Cows, Covered Bridges, and Maple Syrup, to name a few. All of these things attract visitors from the northeast US and the entire globe. Although lesser talked about, the Vermont town is the glue the binds everything, and it is truly what draws visitors to the State. Within Vermont’s borders are 251 towns and villages. These towns make up the heartbeat of the State. They are where the residents live and work, and it is where the charm that attracts visitors is created and housed. If you wish to view a complete list of all 251 towns – click here.

To a visitor, many of these towns may seem similar. A quick drive through most reveals a tree-lined green at the center of town, a white-clappered meeting house and/or church, maybe a covered bridge or two. Some towns are known for a particular activity or attraction, such as a “ski town” or “farm town.” While all of these towns are unique in their local population and design, a few stand out for their beauty, history, tourist appeal, and location. Towns such as Manchester, Stowe, Woodstock, and Middlebury fit that description. I want to talk about my favorite – Woodstock.

It seems that almost every state in the US has a town named Woodstock, with New York’s being the most famous. Vermont’s version is in many ways a quintessential Vermont town featuring a covered bridge, a picturesque green, a quaint village for dining and shopping, and plenty of historic country inns for comfortable lodging. Everything is placed exactly in the right location, and those looking for laid-back country living will be satisfied. These items just scratch the surface, with a big payoff for those willing to do a little exploring Woodstock, and its surrounding area makes for an excellent photographic experience.

The town of Woodstock and the village that sits at its center was founded in 1761. It quickly became a popular location for entrepreneurs, artisans, and manufacturing and quickly became one of Vermont’s largest towns. The population declined throughout the mid-1800s until the advent of the railroad helped the town rebound. Woodstock became a popular stopover for those traveling between Albany, New York, and Boston. Woodstock’s recent history includes the Rockefeller family, the Western railroad Billing’s family. American Scholar George Perkins Marsh gave birth to the conservationist movement with Man and Nature’s publishing in 1864. Woodstock strives to honor its heritage by embracing its past.

Woodstock is home to Vermont’s only National Park. The Marsh-Billings-Rockefeller Historical National Park sits on the north end of town and is an excellent place to start a photographic journey. The park consists of 550 acres of forest that includes Mt. Tom, which offers complete 360-degree views of Woodstock from its summit. The hikes are not strenuous and can easily be done in a couple of hours. Mt. Tom offers excellent views in autumn of the colorful leaves. This historic park represents Vermont on the 2020 US currency quarter. Woodstock’s town green sits in the middle of the main street in-between west-bound and east-bound traffic. The green offers an excellent view of the town’s most popular covered bridge – the middle bridge. The bridge is not old but offers excellent compositions with plenty of foregrounds and Mt. Tom in the background. Suppose you are into old architecture, the buildings in town date back to the town’s beginning. If flower photography is your thing, the Eshqua Bog Natural Area is a short five-minute ride from the center of town in the surrounding forest. The bog features different flora and an excellent selection of Lady Slippers in mid-June. There is a path and boardwalk to make hiking and viewing easier. The Woodstock area is home to two of the most photographed farms in the world. A couple of miles north of town via country backroad sits the Sleepy Hollow Farm. This farm has been photographed extensively over the years; however, interest has exploded recently since its discovery by the Instagram crowd. A few miles south of town is the famous Jenne Farm. Jenne Farm is a collection of barns placed perfectly along the rolling hills of South Woodstock. The composition elements all work perfectly as if they had been placed there by a photographer. Even Hollywood has noticed, and this scene has appeared in several movies over the years. Expect lots of company here in Autumn.

The surrounding towns of Pomfret, Bridgewater, South Woodstock, Quechee, and Taftsville are not technically in Woodstock’s town, but they are considered to be because of their very close proximity in theory. Pomfret and South Woodstock, and Bridgewater are a vast network of country back roads and should be explored for rural photo compositions. Rolling hillsides, barns, farms, lakes, and streams are accessible and waiting to be photographed. During the Spring and Autumn mornings, mist and fog can enhance these locations. Quechee is just 4 miles away and has many attractions itself. Quechee attracts many photographers and tourists alike. Quechee is home to a gorge that is often referred to as Vermont’s Grand Canyon. It is also home to the headquarters of Simon Pearce Glassworks. Simon Pearce’s glassware is sold in big cities throughout the world, and you can view (and photograph) the craftsmen at work. Simon Pearce also features and highly rated restaurant on-premises that sits directly over a large waterfall and looking directly at the Quechee covered bridge.

Woodstock is built for outdoor activities and plenty of indoor amenities for when it comes time to relax. Hiking, biking, fishing, and horseback riding are some of the most popular. If biking and hiking are your things and you would like some professional help exploring Woodstock, contact Great Freedom Adventures. They offer many tours, and their instructors and guides are very knowledgeable. Woodstock is easily reached by car from airports in all directions. It is a two-and-a-half-hour ride from Albany International Airport, NY, and about the same from Boston’s Logan airport. New York City is roughly a five-hour ride. If you have always wanted to enjoy New England charm, there is no better place to experience it all than Woodstock. Listed below are my ten favorite places to photograph in the Woodstock area and in what preferred season.

  1. Jenne Farm – Autumn
  2. Woodstock Village Green – Winter
  3. Sleepy Hollow Farm – Autumn
  4. Middle Covered Bridge – Spring
  5. Silver Lake – Summer
  6. Summit of Mt. Tom – Autumn
  7. Quechee Waterfalls – Winter
  8. Gold Coast Road (Bridgewater) – Autumn
  9. Eshqua Bog Natural Area – Spring
  10. Cloudland Farm Road

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