Woodstock Vermont: A Guide for a Long Weekend

Woodstock, Vermont’s covered bridges, snowy streets, outdoor trails, historic landmarks and cozy restaurants make it a winter wonderland and the perfect get-away for a long weekend.

As an unapologetic lover of the four seasons, the winter months are the time I like to embrace the cold, get outside for some fun in the snow and take in the natural beauty of the woods. And, if I can then sit down by a roaring fire and drink a glass of wine and read a book, I am pretty much the happiest person on the planet.

Vermont is the “Green Mountain State” and that is true throughout the year. In the summer months, birch, maple and evergreen trees cover the mountains. In the winter months, there are enough evergreens to keep a green hue on the horizon as you drive the beautiful country roads.

The quaint town of Woodstock offers a chance for outdoor activities, culture, great dining and relaxation. Located in the central part of the state, it is a 2.5 hour drive from Boston and less than 5 hours from New York City. You will quickly fall in love as you drive into town from either direction. The historic buildings surrounding the Village Green have the feel of a New England movie set or a Currier & Ives painting, complete with a one-lane covered bridge.

Chartered in 1761, this historic town has inns, a theater, shops, restaurants, historic buildings, a working farm within walking distance of town and a Laurance Rockefeller estate.

You will quickly find that Woodstock has more than its fair share of great things to do! The question of what to do will depend on how much time you have. Here is a suggested 4 day, 3 night itinerary. I have also provided a list of other activities, so that you can tailor this to your interests, time and the weather.

 

DAY 1: TRAVEL DAY AND GET TO KNOW THE TOWN DAY

Plan to arrive in Woodstock by lunchtime. Staying at The Woodstock Inn will put you in the middle of town and close to everything. The Inn has several restaurants, lots of seasonal activities and a LEED certified spa. The Woodstock Inn, dating from 1793, was originally a Tavern. In 1830, it became The Eagle Hotel. In 1967, Laurance Rockefeller purchases The Woodstock Inn to be part of the “Rock Resorts”–eco-friendly resorts in various parts of the US and Caribbean.

After arriving, you can park your car, store your luggage and tour the hotel at your leisure. There are many places to sit near a fireplace and read a book.

Or, you can wander into town to get an idea of the area and the shops. I would suggest having lunch at Mon Vert Café on Central Street. The Café serves breakfast and lunch. It is organic, locally sourced and adorable.. For lunch, try the Cobb Salad with local bacon or either the Coffeehouse Brisket sandwich or the Maplebrook Mozzarella Sandwich. Everything is delicious!

After lunch, stroll over to the Yankee Bookshop—Vermont’s oldest continuously operated independent bookstore and one of my favorites.  You will find all the latest bestsellers as well as a wonderful display of books about Vermont or written by Vermonters.

Next, stop at F.H. Gillingham & Sons’ General Store. Still family owned and operating continuously since 1886, you will find Vermont made goods from cheese and maple syrup to puzzles or Vermont scenes. Stepping through the door, you will feel as if you have stepped back in time to the days of the small town shops. Not to be missed.

Check out one of Atlas Obscura’s unusual attractions just a few steps away from Gillingham’s. The Woodstock Town Crier Chalkboard is on your right as you head towards the Green. All the activities and events happening in town are written on this board, which also includes a clock and a thermometer.

 

As you walk back to the Inn, stay on the right side of the Green. Directly across from The Woodstock Inn is Middle Bridge, one of Vermont’s iconic covered bridges. If you are like me, you will take many pictures, none of which will do it justice. Walk across the pedestrian walkway to get a delightful view of the Outchatachee River and the view of the backs of the elegant white Federal-style houses that line the Green.

Once you are back at the Inn, check-in and head down to Richardson’s Tavern for a cocktail and a chance to unwind after a long day. You can sink into one of the comfy leather chairs and grab a bite to eat here or walk to the other side of the Reception Area to The Red Rooster. Dinner at The Inn will be relaxing after a long day and either restaurant has wonderful food.

DAY 2: OUTDOOR ACTIVITIES DAY

If you’re an early riser like I am, head down to the Conservatory as early as 6:30 to grab a cup of coffee or tea. You can sit and read the paper in this airy and cheerful room, if you’d like.

For breakfast, head to The Red Rooster or Mon Vert Café.

After breakfast, I would suggest heading out to experience Vermont’s winter activities. If you enjoy downhill skiing, you will love Suicide Six Ski Area. Although the name is daunting, Suicide Six Ski Resort is family friendly and is known as one of the best small ski and snow boarding mountains in New England. There are ski trails for everyone. In fact, about 70% of the trails are for beginner or intermediate skiers. It also has a historic past. The mountain had the first known ski tow when it opened in the winter of 1936 on a former sheep pasture. If you are planning on being there in February, you can participate in the “Face Race” and hike up the black diamond trail “The Face” and then descend on “Easy Mile.” The total distance is 1.5 miles, but it gives you bragging rights that few have.

If you are skiing Suicide Six, don’t miss lunch at Perley’s Pourhouse. Perley Wheeler was the original Lodge keeper and the restaurant is named for him. The extensive menu includes all skiing “must haves” like chili, burgers and mac & cheese, but also includes salad options for a lighter choice. Not to miss are the “Winter Warmer” cocktails. I suggest trying Spike Hot Cider or Perley’s Hot Toddy.

If you are not a downhill skier, you can try cross country skiing, snowshoeing or “fat biking” on the more than 40 km of trails on Mount Peg and Mount Tom. The Woodstock Nordic Center rents all the equipment you need to do any of these activities and will have you ready to go in no time.

Afternoon activities can include Apres-Ski at Suicide Six or perhaps a service at the Spa. A walk around the Village Green during the golden hour is mesmerizing as  the houses and river sparkle in the late afternoon light. 

For dinner, I highly recommend going to The Lincoln Inn for their tasting menu. Just a short drive to the west of town, The Lincoln Inn Restaurant and Inn is a Foodies destination. The chef, Jevgenija Saromova, is Michelin-star trained in Italy, France and England before making her way to Woodstock. The restaurant was voted one of the Best 10 Restaurants by Forbes in 2016. Situated in a Victorian-style Inn, it is steps away from the Lincoln Covered Bridge and the Outauquechee River. It is a unique and incredible culinary experience!

DAY 3: LOCAL EXPERIENCES DAY

After breakfast, take a short, scenic stroll through town to tour Billings Farm.  This quintessentially New England commercial dairy operation also has one of the finest outdoor history museums in the country. Here, you can really get your “farmer on” and interact with sheep, goats, horses and cows. One of my favorite activities is the daily cow milking in the afternoon.

The Museum also includes the 1890 Farm Manager’s house, farm life exhibits and shows an Academy-Award nominated short documentary about the farm and the adjoining Marsh-Billings-Rockefeller National Historical Park.

Although the Rockefeller Estate House is closed in the winter, the 555-acre property is open for snowshoeing and hiking.

After a morning at the farm, jump in your car and head a few minutes down the road to Quechee for lunch at Simon Pearce.

 

Along the way, you’ll pass the Taftsville Covered Bridge. This quintessentially Vermont red one lane bridge has a pull-off area if you want to get out and take a few pictures. Otherwise, continue a few more miles down the road to the Simon Pearce Flagship Store and Restaurant.

Located on the river with a view of yet another covered bridge–the Quechee Covered Bridge and waterfalls, Simon Pearce’s flagship factory, store and restaurant is a great place to visit. You can watch glass blowing demonstrations and then head up to the Arts & Crafts-style restaurant with wooden tables set with Simon Pearce china and glass. Food at The Mill at Simon Pearce is locally sourced and you will eat with a view of the beautiful bridge and waterfall. I go at least once and year and it is always a wonderful meal and experience. Reservations are suggested for lunch and dinner.

After lunch, Quechee Gorge is less than two minutes away. You can park at the
Visitor Center. There is a path that is sometimes icy, but if not, venture down it to see the reservoir and river.

If you are still in the mood to explore after that, there are several nearby activities. The first is the Vermont Institute of Natural Science (VINS) where you can see and interact with birds of prey (yes, really!). If you’re not full from lunch, my second suggestion is to head to Sugarbush Farm to taste cheeses and maple syrup, all made there. The third, another 15 minute drive, but very worthwhile, is the Montshire Museum of Science. In February, the museum has an annual Igloo Build. But any time of year, it is a fantastic hands-on science museum that everyone will enjoy.

After a full day, The Woodstock Inn will be a perfect place to relax by the fireplace, enjoy a spa treatment or enjoy afternoon tea in the Conservatory.

For a more casual dinner, try The Worthy Kitchen. Calling itself a craft beer and farm diner, it’s the perfect place for a burger and a beer. If you would like a more formal meal, head to The Prince and the Pauper. The cozy, elegant, quintessentially New England décor will complement the food.

DAY 4: LAST TASTE OF VERMONT AND TRAVEL DAY

If you haven’t done so already, it’s your last chance to taste locally grown and produced Vermont Maple Syrup. So, order those pancakes or waffles and enjoy the local flavors at Mountain Creamery! If you haven’t seen the famous Paul Revere bells yet, take a leisurely stroll around town to the landmarks where they are located. Or, walk to Billings Farm, checking out the houses and doors on the way, to see if the animals are getting some fresh air. When you leave, be sure to drive around the Town Green one more time to take in the charming buildings and covered bridge. You won’t forget this idyllic scene. Woodstock is a town that will stay with you for a long time.

 

Things to Do in and around Woodstock

Outdoor Activities

• Suicide Six Ski Area The name belies the family friendly and “best small ski and snowboarding mountain” that is an eight minute drive from the Woodstock Inn. There are ski trails for everyone. It’s the perfect place if you don’t’ want to venture far or if you are with others who are various levels.

• Mount Tom Access to Mount Tom’s trails which are used for cross-country skiing and snowshoeing in the winter are a short walk from the Village Green. The path starts behind the covered bridge. A half hour snowshoe hike up to the top of the hill will provide stunning views of the town. You can rent snowshoes, skis or “fat bikes” at the Woodstock Nordic Center.

• Marsh-Billings-Rockefeller National Historical Park The only national park in Vermont, it was the first to concentrate on conservation. The 555-acre grounds include a mansion (closed in the winter), gardens and carriage roads that are transformed into hiking, snowshoeing and cross-country skiing trails in the winter. George Perkins Marsh was a congressman and diplomat, whose booked entitled Man and Nature, was published in 1864 and was about humanity’s use and abuse of land. Frederick Billings (the grandfather of Mary Rockefeller) owned the property but it was Laurence Rockefeller who gave it for all to use. You can rent equipment from the Woodstock Nordic Center to use the grounds.

• Killington Ski Resort About half an hour’s drive from Woodstock is Killington Ski Resort. Killington has six peaks, 212 trails and 29 lifts. It has kids’ programs and trails for all levels of skiers. In addition, it also has tubing, snowmobiling, sleigh rides and two great venues for life music: The Wobbly Barn and The Pickle Barrel. It’s an easy and beautiful drive from Woodstock and the skiing is some of the best of the East Coast.

• Sleigh Rides There are two venues offering dreamy sleigh rides through the Vermont landscape. Billings Farm offers rides from November through March over the farm’s snowy fields pulled by two of their beautiful work horses. You can even reserve a private sleigh ride for a more romantic adventure. The Woodstock Inn offers daily traditional sleigh rides of South Woodstock through the amazing wintery landscape.

Historical and Cultural Activities

• Billings Farm and Museum One of the oldest dairy farms in the US, this working farm has so much to offer. Just a short walk from the village, you can pet baby cows, tour the original, restored 1890 farmhouse, see modern exhibits of farming techniques and technology and sample raw milk cheese. Oh! And did I mention that you can take a sleigh ride around the beautiful fields? It’s a fantastic place and you will be there much longer than you anticipated, so plan accordingly!

• Paul Revere Bell Tour Paul Revere is, of course, known for his part in the early history of the foundation of our country, but his job as a bell maker lives on today. Woodstock has six bells manufactured in the foundry that Paul Revere established. Three of them are still being used in town. Those in use are in several of Woodstock’s churches: The Masonic Temple (formerly the Christian Church), St. James Episcopal Church and the North Universalist Chapel. A fourth bell is in the south entry of the First Congregational Church because a crack was discovered in it in 1974 that could not be repaired. The fifth bell is located on a pedestal behind the Woodstock Inn in front of the hotel’s putting green. Woodstock Country Club has the sixth. There are guided tours of the bells, but it is easy to map out the route on your own and see them at your own pace.

• Woodstock Town Hall Theatre Originally known as the Woodstock Opera House, the Woodstock Town Hall Theatre does not look like a “country” theater. Its beautiful two-story white columns and brick exterior look formal enough to be put in downtown Boston. The theater is still active today and not only shows current and classic films but also conservation film series and hosts live performances.

• The Norman Williams Public Library Built in 1883 out of pink sandstone, the Norman Williams Public Library was a gift to the town from Dr. Edward Williams and built on the home of his parents. The library has a History Room, a children’s area and a Reading Room, complete with a fireplace. It is an historic place that should not be missed.

• Covered Bridges  There are three covered bridges in and around Woodstock. Middle Bridge across from the Village Green.  Taftsville Bridge on the road to Quechee and the Lincoln Covered Bridge, located to the west of Woodstock on the way to Killington.

• Woodstock Town Crier Chalkboard Mentioned in the Atlas Obscura this historic chalkboard, located in between the Gallery on the Greene and F.H. Gillingham & Sons’ General Store, lists all the activities and events happening in Woodstock.

• Woodstock Vermont Film Series at Billings Farm On many Saturdays from October to May, the Farm hosts the Woodstock VT Film Series, inspired by the environs and focused on films that will “transport viewers to distinctive cultures and destinations that share a strong sense of place.”

• Vermont Institute of Nature Science (VINS) This environmental gem focuses on education, research and avian rehabilitation. There are daily Raptor chats, reptile encounters, raptor feeding times and more. You can see a huge variety of birds who would not survive in nature, but who have modern and well-designed enclosures. Worth the trip.

• Montshire Museum of Science Just a 15 minute drive from Simon Pearce and 25 from The Woodstock Inn, this science museum is recognized as being one of the best in the country. The original museum was started after Dartmouth College closed its natural history museum in the 1970s in a former bowling alley. It is now located on a 100-acre site along the Connecticut River and offers over 150 exhibits relating to natural and physical sciences, ecology and technology.

Places to Stay

• Woodstock Inn and Resort On the village Green, this historical Inn is out of a Currier & Ives painting. With several restaurants, as well as a Spa, the Woodstock Inn and Resort is THE place to stay in and around Woodstock.

• Lincoln Inn and Restaurant A “Culinary Destination”, the Lincoln Inn is on the west side of Woodstock, a short drive from the village. The Lincoln covered bridge is next to the property and situated next to the river, it is a beautiful old inn. With only six rooms, you should book in advance. The restaurant was voted by Forbes magazine as one of the 10 best restaurants of 2016.

• 506 On the River Inn A five minute drive from the Village Green, 506 On the River Inn was recognized by Conde Nast Traveler as one of the Best New Hotels of 2015. The Inn offers rooms with views of the river, Farmhouse suites, country breakfasts and a pool and sauna.

Places to Eat

• Bentley’s Restaurant This Woodstock staple is kitty corner to the Village Green. Burgers and salads as well as dancing and music on the weekends makes this a popular place.

• The Lincoln Inn Voted as one of the 10 Best Restaurants by Forbes Magazine in 2016, the daily prix-fixe dinner is not to be missed. Reservations are a must.

• Long Trail Brewery Just a 10 minute drive or cab ride from downtown Woodstock, see Vermont’s most famous beer made and then try one with a burger or other casual fare.

• Mountain Creamery As well as serving hearty breakfasts and lunches, Mountain Creamery is best known for its Homemade ice Cream, sundaes and frappes. And, yes, you can get it for breakfast.

• Mon Vert Café Modern, organic breakfast and lunch fare as well as good strong coffee. Highly recommend this quintessentially Vermont place.

• Perley’s Pourhouse If you’re skiing Suicide Six, don’t miss this great spot for lunch. Great food and drinks with all the skiing “must haves” like chili, burgers and mac and cheese.

• The Prince and the Pauper One of Vermont’s finest restaurants, the restaurant is a short walk from the Woodstock Inn. They offer both a prix fixe and a Bistro menu. If you are looking for a romantic, candlelit dinner, this is the perfect place.

• The Red Rooster The Woodstock Inn’s place for breakfast, lunch and dinners from Wednesday to Sunday, the menu has something for everyone and the atmosphere is elegant but relaxed. The perfect place for breakfast if you’re staying at The Woodstock Inn.

• Richardson’s Tavern A wood-paneled Tavern within The Woodstock Inn, the menu ranges from oysters to salads to burgers to coq au vin. There is something for everyone here. On Sundays, the brunch menu includes a Bloody Mary bar. Yes, please!

• The Mill at Simon Pearce One of my favorite places to eat, and voted one of “America’s Most Romantic Restaurants” by Travel & Leisure, the restaurant offers fresh local foods with a spectacular view of the Ottauquechee River, waterfalls and covered bridge. Lunch and dinner are served daily. Reservations are recommended.

• Worthy Kitchen A “Craft Beer and Farm Diner”, this is another of my favorite restaurants. From buttermilk fried chicken to a farm burger, the menu changes seasonally and is based on what can be sourced locally. The rustic furnishings—wooden tables and metal chairs means you won’t feel uncomfortable if you don’t want to change out of your ski clothes.