10 Things To See In Woodstock, Vermont On A First Time Visit

The tiny town of Woodstock in central Vermont epitomizes a captivating and quintessential New England village filled with attractive historic buildings and a relaxing aura. Descriptive words like quaint, charming and picturesque can be overused at times. But we think the extraordinarily idyllic town is all of those adjectives, with a splash of enchantment and a dash of irresistible appeal thrown in for good measure. So how do you make the most of your visit?

In this guide we show you our 10 favorite things to do in Woodstock, Vermont including why it’s worth adding to your New England travel itinerary. It’s a place you take things slowly, enjoy the finer things in life and appreciate the colorful leaves rustling in the wind.

Our Experience

We’ve visited Woodstock, Vermont twice, once in 2020 and then again in 2023. Both times we included it on a New England fall road trip. Visiting in 2020 during the height of covid proved challenging for a variety of reasons. But Woodstock was still extremely busy which surprised us. During this trip the weather was overcast, but the fall colors were magnificent and we got to experience many of those eerie autumn foggy mornings.

Since we spent our first trip photographing the town and surrounding area, in 2023 we extensively explored the Billings Farm as it was closed the first time we came. The weather was perfect with bright blue skies and we also enjoyed browsing the shops downtown. For both trips, we thought one day was enough to see Woodstock, but it all depends on your itinerary. Read more about us.

SHOP: Our New England Guidebook features the best of Woodstock and other popular spots in the region.

Now, let’s explore this beautiful area! Here’s where you should go:

1. Admire The Photogenic Barns

One of the most popular things to do in Woodstock is drive around and explore the country roads to find magazine front cover scenes of historic barns. But visitors in recent years have become a major problem for the owners of these older barns. In 2020, we photographed both of these barns and minus a few other serious photographers, these locations were very quiet. There even used to be signs showing photographers where to stand to get an iconic New England picture.

But social media made these barns popular almost overnight and the locations quickly became overrun. During our 2023 visit, many of the roads leading to these barns were closed to public to help eliminate the bad behavior. In truth we almost took this section out of our guide, but these beautiful barns are what makes Woodstock unique. So even if you can’t visit, we thought it was still important to know they exist. As an alternative, you can easily visit the other picturesque sites we list in our guide.

Here are some of the best barns in Woodstock:

• Jenne Road Farm – One of the most photographed barns in the world. It has appeared in television ads, several New England calendars and even a scene from Forrest Gump.
• Sleepy Hollow Farm – Another one of the most photographed locations and nestled within the rolling hills. In autumn, the fallen leaves create the perfect foreground and it’s common to see a foggy mist roll in among the buildings.

Travel Tip: If the roads are closed, please do not try to access these barns as they’re located on private property. This is our responsibility as travelers. Many of these farms sell various items such as maple syrup and buying these products is a wonderful way to support them.

2. Billings Farm And Museum

If you’re traveling with kids, a popular Woodstock activity is the Billings Farm. It was established in 1871, but it’s more than just a farm. Even as adults, we loved exploring the property learning about Vermont farming from the late 1800’s to present day.

The Billings complex is a fully-operating Jersey dairy farm with various educational exhibits and interactive programs. You can pet the animals, walk around the farm manager’s house, stroll a riverside path and enjoy the gardens. We thought the views on the property were stunning and it was nice to go at our own pace because the museum is self-guided. To get to the farm, you can either drive or walk from downtown Woodstock about 0.5 miles away.

Tickets cost $19 for adults and $12 for children 3-15 years of age. Children under 2 are free. Reservations are not required, but you can book online here. The farm is open from 10:00am to 5:00pm everyday from the end May to the end of October with shorter hours in winter. Parking is free and there are two separate lots. The main parking lot is next to the visitor center and the overflow lot is located across the street from the main lot with space for larger vehicles such as RVs.

3. Marsh-Billings-Rockefeller National Historical Park

Perhaps surprisingly for this region in Vermont and New England, Woodstock is not quite as colonial as you might imagine. In fact, you’ll find a wonderfully diverse array of 18th and 19th century architectural styles just from exploring the immediate local area. From pristine Georgian symmetry to palladian style windows of the Federal architectural style and colonial revival showcased by the Marsh Billings Rockefeller house.

Directly across the street from the Billings Farm, the Marsh-Billings-Rockefeller National Historical Park is now run by the National Park Service (NPS). This 643 acre plot of land is named after all of the previous owners of an old dairy farm and forest. In 1992, the land was transferred by the Rockefellers which officially gave Vermont its only unit within the US national park system.

One of the most popular things to do here is to take a guided tour of the beautiful Marsh Billings House. Tours cost $9.00 and must be booked well in advance because they sell out quickly. You can book on Recreation.gov and without a tour, you won’t be able to enter the house. Unfortunately, we could not get tickets for a tour both times we visited, but we still explored stunning property. There are 20 miles of carriage roads winding through 400 year old trees with easy access for hiking in Mount Tom Forest. Visit the official website here for more information.

4. Shop Locally

The picturesque downtown is without a doubt one of the most well known things to do in Woodstock. It’s filled with small independent stores, bookshops, galleries and cafes perfectly arranged along two very pedestrian friendly streets. Supporting local businesses is paramount to the continued prosperity in a touristy town like Woodstock. So don’t be shy about buying an adorable Vermont souvenir and popping in for a coffee at Mon Vert or Soulfully Good.

Here are the popular stores in Woodstock:

• F.H. Gillingham and Sons – An 1886 family run general store selling maple syrup, cheese, gifts and more
• Splendid Bakes – Hidden off the Green, this little joint sells delicious pastries and paninis
• The Yankee Bookshop – Established in 1935, this is Vermont’s longest-running independent bookstore
• Vermont Flannel Company – Organic and ultra-soft flannel clothing since 1991
• Woody’s Mercantile – A unique selection of creative gift ideas

We had a fun time in the Yankee Bookshop because they were carrying Gestalten’s Great American Road Trip. Over 30 of our USA photographs are spread throughout the entire book and it’s always exciting to see. We’re the couple in the hot tub if you look at the listing and 3 out of 4 photos on this cover were taken by us with a picture of Woodstock on the very bottom!

Mark broke his sunglasses during our road trip and we have to give a big shout out to the staff at Eyes on Elm. Not only were they incredibly nice, but they fixed Mark’s sunnies for free. The shop is adorable and they have a lot of interesting lenses. If we were local, this is a place we’d always go so check them out and tell them we sent you!

READ: Most beautiful places to visit in Vermont

5. Woodstock Village Historic District

Since 1973, the entirety of Woodstock Village Historic District has been listed on the National Register of Historic Places, which says enough in itself. You just know this is going to be a remarkably charming section of town. It spans 275 acres and an impressive 95 buildings, but it’s focal point is centered around the elliptical center at the intersection of Vermont Route 106 and US Route 4.

Lying between North and South Park streets, this area is known as The Green. It’s essentially Woodstock’s front yard and the center of the community. The Green is home to the Woodstock Farmer’s Market open from early June to mid-October on Wednesday evenings from 3:00pm to 6:00pm.

We found The Green to be a great place to escape the crowds. The beautiful Norman Williams Public Library and Woodstock Town Hall Theater can be found here along with several of Woodstock’s most impressive stately homes. Not far from The Green before you reach Elm Street, there is also the famous Woodstock Town Crier that historically contains news, events and shoutouts on a simple black and white chalkboard.

Travel Tip: Free parking is offered on the north side of The Green.

6. Find The Covered Bridges

Vermont is home to more covered bridges per square mile than any other US state and Woodstock is one of the best places to set up base for a bridge hunt.

The good news is you don’t even need to leave town to see your first example of a stunning covered bridge. The gorgeous dark wooden colored Woodstock Middle Covered Bridge is smack-dab in the center of Woodstock, right on the edge of The Green. It’s located on Mountain Ave, crossing the Ottauquechee River. Personally, we thought Woodstock Middle Covered Bridge was one of the most visually appealing of all the bridges we saw in Vermont. Not all bridges have pedestrian access, which makes this particular bridge in town one of the things you can’t miss when in Woodstock, VT.

Taftsville Covered Bridge was built in 1836 and is the oldest standing example of a historic covered bridge in Vermont, which makes it a dead-cert on your Woodstock itinerary. It’s 189 ft long and has an attractive classic red colored exterior. A small dam and waterfall along the Ottauquechee River are located just to the northwest side of Taftsville covered bridge as you look at a map. You can park up on Old River Road and walk down a riverside path to open up incredibly photogenic views looking back at the bridge and waterfall.

If that’s not enough, here are a few more in the immediate area:

• Quechee Covered Bridge – About 8 miles east of Woodstock
• Lincoln Covered Bridge – About 3.5 miles southeast of town
• Cornish-Windor Covered Bridge – 15 miles south in the town of Windsor

READ: How to find the best covered bridges in Vermont

7. Go Hiking

Most visitors to Woodstock will pass through in a day or maybe two, which makes finding time for a hike difficult. Especially when there are plenty of amazing hikes in other parts of Vermont such as the adventurous town of Stowe to the north. But for those who do have time for a hike on a longer visit, there are a handful of great options right near town and remember, Woodstock is very close to the Appalachian Trail.

Here are a few of the popular hikes in Woodstock:

Mount Tom and The Pogue – The most sought after trail in Woodstock is within Marsh Billings Rockefeller National Historic Park. You can access Mount Tom via multiple entrances and trailheads but we’d suggest starting at the parking lot near Billings Farm and Museum. The full loop including both The Pogue (pond) and Mt Tom (Woodstock town views) is just over 4.0 miles with 650 ft elevation gain.

Mount Peg – This short 1.3 mile roundtrip loop gains around 300 ft in elevation to provide views looking back over Woodstock, but with views overlooking the south side of town.

Luce’s Lookout – Set your google maps for ‘The Lookout Trailhead’ and drive a quick 8 miles north up VT-12 before turning onto Greengate Road. This is a 2.5 out and back trail with old lookout at the top providing more excellent valley views.

Woodstock Aqueduct Trails – This time set your google maps for ‘Aqueduct Trails’ and a 2.7 mile drive through west Woodstock will bring you to the trailhead. You can choose how far to hike through forest with boardwalks. Be aware that this is primarily a mountain bike trail.

8. Try Some Vermont Products

What’s a trip to Vermont without sampling some delicious homemade maple syrup and cheese. This is exactly what you need to add to your Woodstock bucket list. The Billings Farm we mentioned above sells it’s own ice cream and snacks in the Farmhouse Scoop Shop, but for a more traditional Vermont feel, we also recommend the places below.

• Sugarbush Farm – Offering free admission and tastings featuring 15 different kinds of cheese and 4 grades of maple syrup. You can also take a maple syrup self guided tour with information about tapping sap lines and boiling houses. The farm is open everyday from 9:00am to 5:00pm.
• Plymouth Artisan Cheese – America’s oldest cheddar cheese located in Plymouth about 15 miles southwest of Woodstock.
• Vermont Farmstead Cheese – A delicious variety of artisanal old world cheeses. We love their blueberry windsordale.

Fun Fact: Kristen grew up making maple syrup with her family so we’re very hard critics, but most of the Vermont syrup we tasted passed the test. We even used homemade syrup as guest favors for our wedding.

9. Stay At The Woodstock Inn

The Woodstock Inn is the place to stay in town if you’re celebrating something special or have one final splurge in your New England travel budget. From both the outside and inside, the Woodstock Inn oozes class. It’s perfectly located right in the center of The Green in town, ideal for walking to everything you might need throughout your stay.

>> Book Woodstock Inn: Direct | Booking.com

As you can guess, the Woodstock Inn isn’t cheap, but there are plenty of other lodging options to stay at during your time in Woodstock. You can either read our complete guide to the 7 best hotels in Woodstock VT on our sister site Best Hotels Anywhere, or click on any of the top rated hotels in town below to see availability for your dates:

• The Village Inn of Woodstock
• Sleep Woodstock Motel
• 506 on the River Inn Woodstock
• The Woodstocker B&B
• Woodbridge Inn B&B
• Jackson House Inn

Travel Tip: Even if you don’t stay at the Woodstock Inn, we think it’s still worth checking out. You can grab a drink at the bar, shop the boutiques or enjoy the beautiful spa.

10. Popular Sites Nearby

There are a few things you can do near Woodstock certainly worth your time. These next few attractions are not located within Woodstock, but they are only a short drive away making them a perfect day trip option.

Dartmouth College is located just over the New Hampshire border in Hanover on the other side of the Connecticut River. The Ivy League college is the ninth oldest US institution of education, welcoming students since 1769. It’s about a 20 mile drive east of Woodstock.

Conveniently, the King Arthur Baking Company sits right on the other side of the bridge connecting Vermont and New Hampshire near Dartmouth. This is their flagship location and it features a baking school, cozy café and retail store selling all the bread products you could ever want. We loved sampling the local jams and maple syrup here.

Quechee is a another popular stop along the typical Vermont or New England road trip. Many only visit the Quechee Gorge bridge before moving on to Woodstock. But we highly recommend you set aside more time to walk along the easy gorge-side trail and visit the village of Quechee itself afterwards. Views over Quechee Gorge are best from the bridge, but the gorge-side walk is still picturesque and worth 15 or 20 minutes to blow off the cobwebs.

Once done with the gorge, continue towards Woodstock but turn right on Waterman Hill Road and descend until just before Quechee Covered Bridge. Park up and walk through the pedestrian walkway on this beautiful bridge. To the right you’ll see a collection of boulders in the Ottauquechee River, but the waterfall and dam view is the star of the show. Here you’ll find the highly regarded Mill at Simon Pearce along with a glassblowing studio, which is open to the public.

READ: What to do in Manchester, Vermont

Woodstock Interactive Map

Use our interactive map for Woodstock to familiarize yourself with the area. Click to activate the map. We’ve included the best things to see and do that we already mentioned in this guide.

Map key:

• Red – Our top attractions
• Yellow – Hikes
• Purple – Local stores
• Dark Blue – Hotel recommendations

You can also open the full map here for a better and larger view.

Our Woodstock Photos

We always enjoy our time in Woodstock and take way too many photos. Here are a few of our favorites:

The Morgan Conclusion

What we like: Woodstock is a quaint town and it’s a must-see stop on any Vermont road trip. The main sections downtown are easily accessible and you can see a lot in a short amount of time without having to drive far. We also really enjoyed finding the covered bridges in the area and visiting the Billings Farm because it’s a great place to learn about farming in Vermont.

What we don’t like: Similar to the other picturesque towns in Vermont, Woodstock is incredibly busy in the fall season to a point where it’s almost unbearable. The town is small and it’s extremely overwhelming at times. It’s also very expensive for eating and hotels so you’ll need a healthy budget when you come to town.

Is Woodstock worth visiting? Yes, Woodstock is definitely worth visiting. It’s an adorable travel destination offering a lot of bang for your buck. But it can be very busy so if you visit in peak fall season, mentally prepare for crowds. We found most people hung around downtown so try to visit the attractions not on the main strip. If you want to eat in town, you should also make a reservation if possible.

More From New England

• What to experience in Stowe, Vermont
• Cool activities to do in Manchester, VT
• Popular things to do in Burlington, VT
• Where to find Vermont’s covered bridges
• Things you shouldn’t miss in Acadia National Park
• Best places to stay in Bar Harbor
• 13 amazing stops along NH’s Kancamagus Highway
• How to hike to the Flume Gorge waterfalls
• Tips for planning a New England fall road trip

Want more Vermont content? Head to our Vermont Travel Guides to explore more from the Green Mountain State.

---

We hope our guide featuring the best things to do in Woodstock helps with planning your visit!

Please let us know if you have any questions about visiting Woodstock or planning a trip to New England in the comments below.

Happy Travels,

Mark and Kristen

Enjoy this Woodstock, Vermont guide? Pin it for your visit!

Note: This article contains affiliate links. When you make a purchase using one of these affiliate links, we may earn a small commission at no extra cost to you.

All Rights Reserved © Where Are Those Morgans, LLC. Republishing this article and/or any of its contents (text, photography, maps, graphics, etc.) in whole or in part is strictly prohibited.