Woodstock Travel Guide
The Woodstock Inn & Resort, Woodstock, Vermont
Home to Vermont’s Most Beautiful Address
Picture this: snow is softly falling, collecting on pine branches and the roofs of colonial houses. You walk into the lobby of a beautiful inn after a snowy stroll around the village green, and are immediately warmed by a roaring fire. You make your way into a cozy tavern, grab a seat by another fire, and order a glass of pinot noir. As you sink into the leather armchair, you listen to the quiet chatter of other guests recounting their days’ snowshoe or cross-country skiing adventures.
No, this isn’t a dream, or a scene out of White Christmas. It’s just another day at the Woodstock Inn & Resort in Woodstock, Vermont, also known as “Vermont’s Most Beautiful Address.” This idyllic New England village is perfect for a snowy escape or leaf-peeping pilgrimage, so be sure to add it to your bucket list ASAP.
A Few Things to Note
One weekend is all you need to explore this beautiful little town, especially if you live in New England. If you’re coming from farther away, you might want to bake in an extra day/night for travel.
While the Village of Woodstock is small and easily walkable, you’ll want a car to explore the surrounding area. The good news is you’ll likely have one since the nearest major airport is one hour and 40 minutes away.
During leaf-peeping season especially, please respect people’s privacy. Many private homes have gained a lot of attention on social media, which has led to hordes of tourists trespassing on private property to try to snap pictures. There are plenty of beautiful public places to enjoy the foliage, so stick to those and adhere to posted signs.
Woodstock is an incredibly dog-friendly destination (and Boris-approved), so be sure to read on for recommendations on what to do with your furry friend!
Best Time to Visit Woodstock
Woodstock is beautiful year-round, but I especially love it in the fall and winter. The best time to see peak foliage varies every year depending on many factors including temperature and moisture. That can make it hard to decide when to plan a fall getaway, especially because many accommodations book up a year in advance. With that being said, early to mid-October is usually a safe bet. I love this Fall Foliage Prediction Map and reference it every year when planning trips or day hikes. It is important to note that Woodstock is usually mobbed with tourists most fall weekends, so if you can swing it, you’re better off visiting during the week.
Woodstock, Vermont in early October
We stayed at the Woodstock Inn & Resort in mid-January and it was the perfect cozy winter getaway. We were lucky because there was already snow on the ground when we got there, and then we woke up to a snowstorm the following morning. While it’s hard to predict, February is typically the snowiest month in Woodstock. What’s nice about visiting in January is you can still enjoy Christmas lights and decorations.
Boris enjoying Woodstock winter
Wedding season is in full swing during the summer months, so don’t be surprised if popular accommodations are sold out almost every weekend. If you are able to snag a room somewhere, you can enjoy activities like golf (May-October) and fly fishing (April-October).
How to Get to Woodstock
While some hotels will help you arrange a private car service, the best way to get to Woodstock is by car. Here are the driving times from nearby cities:
Burlington, VT: ~1.5 hours
Boston, MA: 2.5 hours
New York, NY: 5 hours
Manchester, NH: ~1.5 hours
And here are the closest airports (where you can also rent a car):
Burlington International Airport (BTV)
Boston Logan International Airport (BOS)
Manchester-Boston Regional Airport (MHT)
There’s also a small airport in Lebanon, NH (about 30 minutes away), but Cape Air is the only airline that flies into there. There are two rental car companies here (Avis and Enterprise).
Where to Stay in Woodstock
The Woodstock Inn & Resort
Woodstock Inn & Resort ($$$) - With a history that dates back to 1793 and includes the Rockefellers, the Woodstock Inn & Resort is quintessential Vermont. It’s located just off The Green in the Village of Woodstock and as you pull up, you’re greeted by an impeccably manicured front lawn and a majestic white building. The interior is just as gorgeous as the exterior, and the design of the lobby, restaurants, guest rooms, and spa is drool-worthy. It’s also the best pet-friendly hotel I’ve stayed in! A certain number of rooms on the Garden Level are dog-friendly, and they’re conveniently located right near the exit/dog walking area. They’ll even put an Orvis dog bed and bowl in your room. We felt so welcome, and everyone loved Boris. I lost count of how many times we stopped by the front desk and sat patiently waiting for dog cookies, to which the kind women working there lovingly obliged. Petition to make Boris the official mascot of the inn?! Talk about a dream job…The food was delicious (more on that later), but I’d be remiss to not call out the spa. The Spa at the Woodstock Inn & Resort is one of the most beautiful I’ve ever been to, and it’s LEED-certified and Forbes-rated. My husband and I got a couples massage, and then enjoyed the dry-cedar sauna and outdoor heated whirlpool. The facilities are top of the line, and it was heavenly to sit in the hot, bubbling water, totally relaxed, as snow softly fell all around us.
Book with me to enjoy exclusive perks like breakfast for two daily, hotel credit (can be used towards spa services!), a welcome amenity, room upgrade (subject to availability), and more!
Boris making himself right at home at the Woodstock Inn & Resort
Twin Farms ($$$$) - While technically located less than 20 minutes outside of Woodstock in Barnard, Twin Farms is Vermont’s only five-star hotel. It has an impressive list of accolades including Forbes Hotel of the Year, Conde Nast Top 50 Resorts in the World, Travel + Leisure World’s Best, and more. Set on 300 private acres are 28 individually designed rooms, from treehouses to cottages to farmhouse-style suites. The price tag is steep (starting at $2,700/night), but everything is included: all meals, wines, spirits, and activities. From canoeing on their private pond to pasta making classes, Twin Farms is the ultimate luxurious Vermont escape. I haven’t stayed here, but it’s on my Vermonter bucket list. They also allow dogs up to 100 pounds, so I guess Boris will have to come too!
Book with me to enjoy exclusive perks like a special gift set valued at $140, early check-in/late check-out (subject to availability), and more!
Where to Eat & Drink in Woodstock
The Red Rooster ($$$$) - This award-winning restaurant is located inside the Woodstock Inn and we ate here three times during our stay; once for a post-snowshoeing snack and beer, once for dinner, and once for breakfast. My husband had an incredible duck special for dinner, and I got the ribeye, which was divine. All ingredients are fresh and local, and the sommelier recommended the perfect red wine to pair with our dinner. Note that reservations are required for dinner. Breakfast is buffet only, but it’s probably one of my favorite breakfast buffets ever. Highlights include cheddar biscuits and gravy, country home fries, and johnny cakes. Note that between 3 and 5:30 is bar service only, but this was a great spot to have a drink and split an appetizer after a day of snowshoeing.
Duck special at The Red Rooster, Woodstock Inn & Resort
Worthy Kitchen ($$) - Craving a good burger? Then make sure you check out Worthy Kitchen, a quick 5-minute drive from The Green. I love the Kitchen Smash Burger and the Worthy Truffle Fries, and they have a great selection of local Vermont beers on tap plus cocktails. Their summer and winter hours are different, so be sure to check their website for the most up to date hours. Reservations not required but recommended (especially for dinner in the winter) as it’s a popular spot!
Mon Vert Cafe ($$) - Located just steps away from The Green is this great breakfast and lunch spot. Whether you’re looking to dine in or grab food to go, they have a ton of options. I love their avocado toast and breakfast burrito, and they have coffee, a full espresso bar, wine, and beer. Hot tip: it gets packed on the weekends, so if you want to grab food to go, be sure to place an order ahead online or by calling.
Richardson’s Tavern ($$-$$$) - Built in 1793, Richardson’s Tavern was the original lodging of the Woodstock Inn. Today, it’s a super cozy pub that serves delicious cocktails and dinner. We grabbed a drink at the bar beside the fireplace before dinner at Red Rooster.
Simon Pearce ($$$$) - Simon Pearce is famous for their handmade glass and pottery. But did you know they also have a restaurant inside a beautiful mill on the Ottauquechee River, just 15 minutes from Woodstock? They serve “creative American cuisine” using fresh, local ingredients. We haven’t eaten here yet, but it’s on my Vermonter bucket list (which seems to keep growing even after living here for five years!) Reservations required, and they can fill up pretty far in advance!
Things to Do in Woodstock
Snowshoe or cross-country ski in Marsh-Billings-Rockefeller National Historical Park - One of my favorite winter activities is taking Boris snowshoeing. I’m sure it comes as no surprise that as a Bernese Mountain Dog, he loves the snow. Whether you have your own gear or rent some from the Woodstock Inn’s Nordic Center, there are plenty of trails to check out. We parked at Billings Farm, located just a half-mile from the inn, and explored the Mt. Tom trails. You can also check out the Mt. Peg trails, which are located near the Nordic Center. Note that you need a day pass to use the trails in the winter since they are groomed and maintained by the Woodstock Inn, and you can purchase one at the Nordic Center.
A very happy mountain dog in Woodstock, Vermont
Fly fish - The Woodstock Inn is an Orvis Authorized Dealer with Orvis Endorsed Guides, and the fly shop is located in the inn’s Activity Center. Whether you’re a beginner or experienced fly fisher, you can book wade or float trips and casting lessons. Even though my husband is an experienced fly fisherman, it’s still so much fun to get a guide as they tie your flies for you and take you to some of the best spots! While you can fish year-round in the area, the season is typically April to October and popular spots to fish include the White River, Black River, Ottauquechee River, Kedron Brook, Barnard Brook, and more. If you do choose to go out on your own, make sure you purchase a Vermont fly fishing license from the VT Fish & Wildlife Department (you can buy one for the day or the year). If you go on a guided trip, they’ll remind you to buy one in the shop before heading out.
Visit one of the local farms - Vermont is famous for its dairy and produce, so why not see firsthand where all of these incredible, locally-sourced ingredients come from? Whether you want to see maple syrup tapping in action, enjoy a farm-to-table dinner, or actually spend a day or two getting your hands dirty, there are a bunch of beautiful farms to visit in the area, including Billings Farm, Cloudland Farm, and Sugarbush Farm.
Billings Farm & Museum, Woodstock, Vermont
Woodstock is quintessential Vermont and beautiful year-round, especially in the fall and winter. It’s the perfect place to escape for a few days as a couple, a family, or with your furry friend. Here are some more of my favorite pictures from days in Woodstock over the years!
The Woodstock Inn & Resort
The best dog-friendly hotel in Vermont! (Woodstock Inn)
Vermont’s most beautiful address and the best suppliers of dog cookies
The Woodstock Inn & Resort
Fall in Woodstock, Vermont
Fall in Woodstock, Vermont
