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Woodstock, Vermont: The Best & Fun Things To Do + Places To Visit (That Aren’t Just Watching Trees Grow)

The village itself is flat and short enough to walk end to end, so the covered bridges and the shops cost you nothing in effort. The climbing starts outside it. Mount Tom and Mount Peg both run steep and rocky, so wear proper shoes and carry water for either. Quechee Gorge drops over 165 feet, and hiking to the bottom is a real descent with a real climb back out. The Ottauquechee River Trail stays level the whole way along.

Welcome to Woodstock, Vermont, a charming town sitting in the heart of New England. Serious eater, nature lover, history reader or somebody just after a slow getaway, Woodstock covers all four. With its picturesque covered bridges, rolling hills and friendly community, it is no wonder that Woodstock draws tourists and locals alike.

One of the iconic sights in Woodstock is its covered bridges. Take a stroll through the village and you will come across the Middle Covered Bridge, Taftsville Covered Bridge, and the Lincoln Covered Bridge. These bridges are functional, but they also stand as a reminder of the town’s history. You can even take a guided tour to learn more about their significance.

When you are not looking over the covered bridges, be sure to work through some of Woodstock’s famous cheese and maple syrup. Visit Sugarbush Farm to sample a spread of cheeses and learn about the process of making maple syrup. For something sweet, stop by the Woodstock Farmer’s Market for some maple candy or fudge. And if you are feeling adventurous, take a hot air balloon ride for a bird’s eye view of the town and the surrounding countryside.

Key Takeaways

• Woodstock, Vermont is a charming town with something for everyone.
• The covered bridges are a must-see sight in Woodstock.
• Don’t leave without trying the cheese and maple syrup!

Charming Woodstock, Vermont

Welcome to Woodstock, Vermont, the epitome of small-town charm. This picturesque village sits in the heart of the Green Mountains and makes a strong place to get clear of the grind of the city.

As you walk along the quaint streets of Woodstock, you will feel like you have stepped back in time. The village is home to carefully preserved 19th-century architecture, including the Woodstock Inn & Resort.

But do not let the historic buildings fool you, because Woodstock is a working town with plenty of modern amenities. You will find a spread of independent shops, art galleries and restaurants, all with their own character.

One of the best things about Woodstock is its walkability. You can easily spend an entire day strolling along the village streets, taking in the sights and sounds of this charming town. And if you need a break from walking, hop on the Woodstock Trolley for a leisurely tour of the area.

No visit to Woodstock is complete without a visit to the Woodstock Farmers’ Market. This local institution has been serving fresh produce, baked goods and other Vermont-made products since 1886. Be sure to try some of the famous Vermont cheddar cheese while you are there.

Outdoor adventures or a slow getaway, Woodstock covers both. From hiking the nearby trails to taking a leisurely stroll through the village, you are sure to fall for the charm of this small town.

The Covered Bridges of Woodstock

If you are in Woodstock, Vermont, you have to visit the covered bridges. You cannot miss them, because there is a trio of them. It is like a three-for-one deal, except you do not have to pay anything. You can just drive around and take in the rustic charm of these bridges.

Bridge Spotting Itinerary

Here is a suggested itinerary for bridge spotting in Woodstock:

1. Start with the Middle Covered Bridge, the most famous one in Woodstock. It’s located right in the village, so you can’t miss it. Take a few photos and cross the bridge to the other side. If you’re lucky, you might see some ducks swimming in the river.
2. Next, head to Taftsville Covered Bridge, which is on the outskirts of Woodstock on the road back to Boston. This bridge has a red color and a unique design. It’s a great spot for a picnic or a romantic stroll.
3. After that, drive to Lincoln Covered Bridge, which is just a few minutes away from Taftsville. This bridge is not as famous as the other two, but it’s still worth a visit. It’s tucked away in the woods, so it’s a great spot for some peace and quiet.
4. Finally, head to Quechee Covered Bridge, which is a bit further west on Route 4. While not a covered bridge, the graceful green beauty of Quechee is still historically important — and breathtaking.

Do not forget to take lots of photos. These bridges are more than structures, because they are part of Woodstock’s history and charm. Enjoy.

Getting Cheesy and Syrupy

You cannot visit Vermont without working through some of the state’s famous maple syrup and local cheese. Luckily, Woodstock runs plenty of chances for you to get cheesy and syrupy.

Start off by visiting Sugarbush Farm, where you can learn about the process of making maple syrup and even taste some of their maple products. If you are feeling adventurous, try the maple cream or maple mustard, because they might just change your life.

But wait, there is more. Sugarbush Farm also runs a spread of local cheeses for you to sample. From cheddar to gouda, the range covers every cheese lover. And if you cannot decide which one to take home, do not worry, because they offer cheese samplers so you can try them all.

If you want to take your cheese obsession further, head over to Billings Farm & Museum. This historic farm opens up Vermont’s agricultural past, but it also runs a cheese-making facility. You can watch as the cheese is made and even sample some of the fresh, local cheese.

And of course, you cannot forget about the maple syrup. Take a trip to a local maple farm and see how the syrup is made from start to finish. You can even bring home a bottle, or two, of the sweet stuff to drizzle on your pancakes back home.

In summary, getting cheesy and syrupy in Woodstock belongs on any list. From learning about the process of making maple syrup to sampling local cheeses, the town covers both. Just be prepared to leave with a full stomach and a newfound love for all things maple and cheese.

Exploring the Outdoors

Woodstock, Vermont is a haven for outdoor enthusiasts. There are plenty of trails, pastures and conservation areas to work through. Experienced hiker or somebody just after a leisurely stroll, the town covers both.

One of the busier destinations is the Ottauquechee River. This picturesque river suits kayaking, fishing and swimming. If you are feeling adventurous, try hiking along the Ottauquechee River Trail. The trail follows the river a long way and opens up long views of the surrounding mountains.

For a harder hike, head to Mount Tom or Mount Peg. These peaks open up panoramic views of the town and the surrounding countryside. The trails can be steep and rocky, so make sure you wear sturdy shoes and bring plenty of water.

If you want a more relaxed day outdoors, head to one of Woodstock’s many pastures. These quiet fields suit a picnic or a game of frisbee. Plus, you might even spot some local wildlife, like deer or rabbits.

And of course, no visit to Woodstock is complete without a trip to the Quechee Gorge. This natural wonder runs over 165 feet deep and opens up long views of the surrounding landscape. Take a leisurely stroll along the Quechee Gorge Trail or hike down to the bottom for a close look at the gorge.

So grab your hiking boots, pack a picnic, and get ready to work through the open country in Woodstock, Vermont.

Historical Sites of Woodstock

Woodstock is a town steeped in history, and you can learn all about it by visiting its many historical sites. Here are the historical sites in Woodstock worth your day:

Marsh-Billings-Rockefeller National Historical Park

If you read history, the Marsh-Billings-Rockefeller National Historical Park belongs on the list. This park is the only national park in Vermont and is dedicated to preserving the history of conservation in America. You can take a guided tour of the mansion and learn about the three families who lived there and their impact on conservation in the USA. And if you are lucky, you might even spot some wildlife on the park’s 20 miles of hiking trails.

Dana House

The Dana House is a fine example of the Federal style of architecture that was popular in the early 19th century. It was built in 1807 and has been preserved to look exactly as it did when it was first built. You can take a guided tour of the house and learn about the history of the Dana family, who were prominent members of the Woodstock community.

Woodstock Historic Sites

If you are interested in learning about the history of Woodstock itself, there are plenty of historic sites to visit. The Billings Farm & Museum is a working farm that has been in operation since the 19th century and is now a museum dedicated to educating visitors about Vermont’s rural heritage. The Woodstock History Center is another one to catch, with exhibits on the town’s history and a research library holding over 2,000 volumes.

Historic Homes

There are also several historic homes in Woodstock that are worth visiting. The Woodstock Inn & Resort is a fine example of Georgian architecture and has been welcoming guests since 1892. The Lincoln Inn & Restaurant at the Covered Bridge is another historic home that has been converted into a bed and breakfast. It was originally built in 1792 and has been carefully restored to its former condition.

National Park Service

Overall, the historical sites in Woodstock open up a fascinating view of the town’s past. Conservation, architecture or local history, the town covers all three. So why not plan a visit to Woodstock today and work through its long history for yourself?

The Woodstock Farmers’ Market has been trading here since 1886. The Dana House went up in 1807 and still looks as it did then. The Woodstock Inn & Resort has taken guests since 1892, and the Lincoln Inn dates all the way back to 1792. Marsh-Billings-Rockefeller is the only national park in Vermont and carries 20 miles of trail. The Woodstock History Center holds a research library of over 2,000 volumes. Quechee Gorge runs over 165 feet deep.

Shopping in Downtown Woodstock

You have come to Woodstock, Vermont, and you are looking for some shopping therapy. Downtown Woodstock answers that, with a spread of shops to work through.

First stop, The Green. This charming park is surrounded by shops and restaurants, which makes it a strong place to start your shopping. Take a stroll and check out the local vendors selling handmade crafts, jewelry and more.

Next, head to Simon Pearce’s flagship store, where you can browse glassware and pottery made on-site. The gift shop is also worth a visit, where you can find unusual items that make strong souvenirs.

If you are a bookworm, do not miss the Yankee Bookshop, Vermont’s oldest continuously operated independent bookstore. Browse their selection of books, including local authors and bestsellers.

For those looking for home decor, Farmhouse Pottery runs a selection of handmade ceramics and other rustic home goods. You will find everything from dinnerware to vases and even soap dishes.

Finally, do not forget to check out the art galleries in downtown Woodstock. You will find a spread of styles and mediums, from traditional landscapes to modern abstracts.

With so many shops to choose from, you are sure to find something that catches your eye in downtown Woodstock. Happy shopping.

Farm Life in Woodstock

Woodstock is a place where you can get a taste of farm life. You can visit Jenne Road Farm and see their farm animals up close. You can even pet them if you are feeling brave enough. Just remember, they are not as friendly as your neighbor’s cat.

If you want to learn more about farming, head over to Billings Farm and Museum. They run interactive exhibits that will teach you about dairy farming and the history of agriculture in Vermont. You can even try your hand at milking a cow. Do not worry, because they will not judge you if you are not a pro.

Speaking of dairy farms, Cloudland Farm is another strong spot to visit. They specialize in grass-fed beef and organic vegetables. You can take a tour of the farm and see how they raise their animals. And if you are feeling hungry, stop by their Dairy Bar for some ice cream.

If you are more of a fruit person, check out the orchards in Woodstock. You can pick your own apples, peaches and berries. Just make sure to wash them before you eat them. We do not want you getting sick.

Overall, farm life in Woodstock is a fun and educational stretch. You will see how food is grown and raised, and maybe even try some fresh produce along the way.

Savoring Woodstock’s Cuisine

When it comes to food, Woodstock covers most tastes. From farm-to-table dining to local cheeses, you will not be disappointed with what this charming town puts on the table.

Start your day with a cup of coffee at Mon Vert Cafe, a cozy spot with a strong selection of pastries. If you are feeling adventurous, try their lavender latte, because it is surprisingly good.

For lunch, head to Worthy Kitchen, a gastropub that specializes in craft beer and comfort food. You cannot go wrong with their famous fried chicken sandwich or their mac and cheese. And of course, do not forget to wash it down with a local beer, because they run over 20 on draft.

If you are in the mood for something fancier, check out The Prince & The Pauper Restaurant. This long-running establishment serves refined global fare in an elegant yet relaxed setting. Their wine list is serious, so be sure to ask the sommelier for a suggestion.

For a taste of Vermont’s famous cheeses, stop by Sugarbush Farm. They run free cheese tastings, so you can try before you buy. Their smoked cheddar is the thing to order.

And if you are interested in herbs, visit the Woodstock Farmers’ Market. They run a deep bench of fresh herbs, as well as other local produce. Pick up some ingredients for a picnic lunch and head to the nearby Billings Farm & Museum for a scenic spot to eat it.

In conclusion, Woodstock’s cooking is not to be missed. Beer, wine, farm-to-table dining, herbs or local cheeses, you will find them all in this charming town.

Woodstock’s Community Vibe

Ah, Woodstock. The charming town in Vermont that is known for its artistic streak, its quirky charm and its open scenery. But what really sets Woodstock apart is its community feel. From fall festivals to live music events, Woodstock has a way of bringing people together and making everyone feel like part of one big family.

First off, let us talk about fall. If you are lucky enough to be in Woodstock during the fall months, you are in for a treat. The town comes alive with foliage, and there are plenty of community events to attend. From the annual Harvest Festival to the Woodstock Vermont Film Series, there is always something going on. And let us not forget about the pumpkin patches and apple orchards. Nothing says fall like picking your own apples and sipping on hot cider.

But the community feel in Woodstock runs far beyond the fall season. Throughout the year, you will find live music events happening all over town. Whether it is at the local brewery or one of the many community centers, there is always a band playing and people dancing. And if you are lucky, you might even catch a performance by one of Woodstock’s talented local musicians.

Of course, no community would be complete without its local businesses. And Woodstock runs plenty of those. From the Woodstock Farmers’ Market to the Unicorn gift shop, there are plenty of independent shops and boutiques to work through. And let us not forget about the restaurants. Gourmet meal or quick bite, Woodstock settles both.

So, if you want a town with a strong sense of community, Woodstock answers that. With its fall festivals, its live music events and its local businesses, you will feel right at home in no time.

Where to Stay in Woodstock

So, you have decided to visit Woodstock, Vermont, and now you need a place to stay. Lucky for you, Woodstock runs a spread of options to fit any budget and taste.

If you want a luxurious stay, the Woodstock Inn and Resort answers that. This historic hotel is the epitome of New England charm, with cozy rooms, serious dining options and a full-service spa. Plus, you cannot beat the location, which puts you right in the heart of Woodstock.

But maybe you are on a tighter budget. Fear not. Woodstock runs plenty of affordable options too. Check out the Shire Woodstock, a cozy motel with clean rooms and friendly staff. Or, if you are feeling adventurous, try camping at the Woodstock KOA. Just make sure you bring bug spray, because those Vermont mosquitoes can be fierce.

Of course, there are plenty of other options in between. The Lincoln Inn is a charming bed and breakfast with long views of the Ottauquechee River. And if you want something a bit more modern, the 506 On the River Inn is a sleek, contemporary hotel with all the amenities you could want.

No matter where you stay, you are sure to fall for Woodstock’s charming streets, friendly locals and open scenery.

Unconventional Woodstock

So you have already checked out the covered bridges and the Billings Farm and Museum. What is next on your list of things to do in Woodstock, Vermont? How about something a little more unconventional?

First up, why not try your hand at falconry? That is right, New England Falconry runs private falconry experiences where you can learn about the ancient sport of hunting with birds of prey. You will handle and fly a trained hawk or falcon, and even watch as it catches its prey. It is an unusual and serious experience that you will not soon forget.

If you want some adventure, Suicide Six might be just the ticket. This ski resort runs skiing and snowboarding in the winter, but also mountain biking and hiking in the summer. And if you are really feeling daring, you can try out their zipline canopy tour, where you will run through the trees at high speed.

But maybe you want something a little more relaxing. How about a dip in the local swimming hole? The Mill Pond Swimming Hole is a busy spot for locals and visitors alike, with clear water and a picturesque waterfall. It is a strong place to cool off on a hot summer day.

And speaking of mountain biking, Woodstock runs some strong trails for all skill levels. Check out the Mt. Peg trails for some scenic views and demanding terrain, or head over to the Aqueduct Trails for some more mellow riding.

Finally, if you want a winter getaway that is a little different, why not try out a yurt? The Woodstock Inn & Resort runs yurt rentals, complete with a wood-burning stove, comfortable furnishings and long views of the surrounding mountains. It is a strong way to get away from it all and sit with some peace and quiet outdoors.

So there you have it, some unconventional things to do in Woodstock, Vermont. Adventure, quiet, or just something a little different, Woodstock covers all three.

Frequently asked questions about Woodstock, Vermont

Which bridge in Woodstock should you actually stop at, and does any of it cost anything?

All three of them cost nothing at all, which is really the whole point of the exercise. The Middle Covered Bridge sits in the village itself and is the one you reach on foot without any planning. Taftsville and Lincoln both need the car. A guided tour is available if you want the history that goes along with them. Otherwise just drive the loop and take the photographs.

Which park near Woodstock is worth the entry, and what exactly do you get for it?

Marsh-Billings-Rockefeller National Historical Park, which happens to be the only national park anywhere in the state of Vermont at all. The mansion tour covers three families and the story of American conservation, and 20 miles of hiking trail run out from it. Billings Farm & Museum is the working-farm alternative, with cheese made on site. The Green costs nothing. Quechee Gorge Trail is free too.

What can you do on the river in Woodstock without spending very much at all?

Swim in it. The Ottauquechee takes kayaking and fishing as well, and the Ottauquechee River Trail follows the water a long way without costing you anything whatsoever. Mill Pond Swimming Hole is the free option that locals actually use, waterfall included. Sugarbush Farm gives its cheese tastings away, so build the picnic around that. The pastures are free.

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