Covered bridges, country inns, and peak foliage make this Vermont town an autumn classic.
By Teddy Danielson
Woodstock is one of America’s prettiest small towns and the perfect place to experience the magic of Vermont fall. I’ve had the honor of getting a local’s perspective on some of the area’s sweetest spots since one of my best friends grew up in Pomfret, Vermont, just a stone’s throw away from Woodstock.
With Mount Tom on one side and Mount Peg on the other, and the Ottauquechee River running through it, the little gem lights up with red and gold leaves in the fall and has no shortage of quintessentially fall attractions and activities. Think fall foliage hikes, scenic drives, covered bridges, maple syrup farms, and cozy bakeries serving up things like apple cider donuts and fresh-baked bagels.
This three-day itinerary is perfect for a long weekend and takes you through some of the best the town has to offer. So pack your hiking shoes, some adventure clothes, a couple of presentable outfits, and enjoy.
Lodging and Transportation
Woodstock is home to many absolutely adorable Inns and B&Bs. Fall is the high season for this maple syrup slingin’ town, so expect slightly higher room rates. Here are a few of my top picks for a long weekend stay in town:
- The Woodstocker B&B: This centrally located B&B offers gorgeous rustic-modern suites, some with their own sauna! Breakfast is included and can be enjoyed in the dining room or in your suite. Oh, and you get to keep the slippers.
- On The River Inn: Another fabulous mid-range option. The inn features spacious rooms, many with views of the Ottauquechee River and each with its own private balcony (or patio). Guests have access to the inn’s indoor pool and sauna. Got your family with you? Book one of their farmhouse suites. Please note that breakfast is not included in your stay; however, you can add it for an additional cost.
- Woodstock Inn & Resort: This is the splurge stay, right in the heart of the village. The rooms have that classic New England feel, and some even have fireplaces. You can book a treatment at the on-site spa, have dinner at Richardson’s Tavern, and use the indoor pool and sauna at the inn’s Athletic Club. Admission to Billings Farm & Museum is included in the resort fee, too!
Every one of these options is fabulous. You’ll notice that several of the items on our itinerary are at (or through) Woodstock Inn. Please don’t worry if a stay at the Inn is out of your price range. You can still enjoy their spa and dining options, as well as book a fly-fishing excursion through their concierge.
Transportation
As much as I love a three-day weekend that doesn’t require you to start an engine, you will need a car for this trip as you will be exploring the areas surrounding the town. If you’re driving to Woodstock from a neighboring town, great. If you’re flying, you’ll want to rent a car. The closest major airport is Burlington International Airport, about a 1.5-hour drive from your destination. Plan on an early arrival so you can get some fun activities in before the day is out.
Friday: Check-In, Cheese, and Covered Bridges
Morning Arrival and Maple Syrup
Day one in Woodstock is all about winding roads through fall colors, covered bridges, and a little cheese tasting. After you pick up your rental car at Burlington International Airport, make the 1.5-hour drive to Woodstock. Drop your bags at your inn/hotel and head on out to one of the more quintessentially Vermont experiences: maple syrup tasting. Grab a quick sandwich from The Village Butcher to go. You’ll need it later. I’m a fan of their house roast beef.
Your first big stop in Woodstock, Vermont, is Bourdon Maple Farm. This 135-acre sugarbush (a forest of maple trees tapped for sap) has been making maple syrup since 1953. They offer tours by reservation only, so be sure to book one in advance. Tours run for about an hour and take you through Bourdon’s sugarhouse with one of their expert sugarmakers. Your guide will explain the tree-to-bottle process of making maple syrup and will end with a maple syrup tasting.
A Late Afternoon of Covered Bridges
A drive through the winding roads of Vermont might be one of the best ways to witness the season’s gorgeous turning leaves. Reds, yellows, and oranges explode across the deciduous forest, made all the more vivid by the crisp fall air. I don’t love driving without a purpose, though, so I suggest stopping to check out some of the region’s historic covered bridges along the way.
Hop in the car and head west to Lincoln Covered Bridge, the first stop on your covered bridge tour. You’ll work your way back to Woodstock from there. Lincoln Covered Bridge is a creaky, one-lane bridge that crosses the Ottauquechee River. It’s been around since 1877 and has a barn-like aesthetic with wooden arches shading its passage.
Drive on through and continue on to Middle Covered Bridge, another crossing of the Ottauquechee River. This one’s much more modern (est. 1969) but has an old-fashioned look. Hop out of the car and admire the river views and the fact that the bridge is held together with wooden pegs instead of nails. It’s just steps from the Village Green, which is a great spot to enjoy that sandwich you brought for lunch.
Up next is Taftville Covered Bridge. This 189-ft., bright red bridge dates back to 1836, making it one of the oldest covered bridges in the country. Next to the reds and oranges of the fall foliage and the sparkling blues and greens of the river below, it’s a great place for a photo before you end your tour at Quechee Covered Bridge. Rebuilt after Hurricane Irene, the Quechee Bridge features a pedestrian walkway and gorgeous views of the old dam waterfall. It’s right next to Simon Pearce, your stop for dinner.
Dinner with a View
Dinner at Simon Pearce is a must on your Woodstock trip. It’s technically in the town next door, Quechee, but it’s only a 15-minute drive back to home base and, since you’re already there, you might as well stop for a meal. Their Maple-Brined Pork Chop is, in my opinion, the perfect fall meal. I also love their Harvest Cassoulet and Vermont Cheese Plate (served with buttery, flaky scones!).
The restaurant overlooks cascading waterfalls over Quechee Dam and doubles as the company’s flagship store. Simon Pearce is, first and foremost, a glassblowing studio producing all sorts of home goods. I love that their turbines are powered by the rushing river below. If you have time before dinner, have a wander through their collection.
After dinner, enjoy an easy, 15-minute drive back to Woodstock and tuck into your inn’s cozy bed.
Saturday: Mount Tom and Woodstock Village
Morning Adventure
Rise and shine! Today’s an adventure day. Throw on your hiking boots (and pack a nice outfit for dinner) before heading to breakfast. Of course, you can have breakfast at your hotel/inn’s restaurant, but I am a big fan of Mon Vert Café. Totally organic, their menu is built on locally sourced ingredients, and the indoor-outdoor atmosphere is casual and cute as can be. Their collection of breakfast sandwiches is a menu highlight, as well as their assortment of local pastries.
After breakfast, head out to Mount Tom in Marsh-Billings-Rockefeller National Historical Park. Yesterday was fall foliage by car; today, you’re experiencing Woodstock’s seasonal beauty on foot. Several trails take you up the stunning Mount Tom, but the Pogue and South Peak loop is my favorite. It’s got some mild-to-moderate elevation gain (for those of you who want a workout) and a section of the trail loops around a 14-acre pond. Round trip, the hike is about 4 miles long and takes the average Joe about 2-2.5 hours. If you are craving a shorter, steeper trek, consider the 1.7-mile Faulkner Trail.
Afternoon Donuts and Spa Time
After your hike, you’ll be ready for lunch. Head to The Woodland Fairy. They have the best selection of fresh bagels, cinnamon rolls, and apple cider donuts in town (in my opinion). I’m a huge fan of their made-to-order Cider Stax (2 apple cider donuts with maple buttercream filling) and their Grilled Cheese (on a fresh NY-style bagel).
After lunch, head back to town. If you have room in your belly, get a scoop of Maple Cream ice cream from Woodstock Scoops before indulging in a luxurious late afternoon at the Spa at Woodstock Inn. Last time I was in Woodstock in the fall, I splurged on the Warm Vanilla Pumpkin Ritual. I just couldn’t resist. Such a distinctly fall option. It involved a pumpkin-spice body scrub, a hydrating wrap, a scalp and foot massage, and pumpkin vanilla body butter. Amazing. If you prefer a massage, I’ve heard their Body Melt Back Therapy is the cat’s pajamas.
Once you’re thoroughly spa-ed out and relaxed, get yourself ready for dinner (remember that outfit you packed before leaving for your hike?) at Richardson’s Tavern. This semi-formal dining option is at the Woodstock Inn & Resort, so you don’t have to go far. Its cozy atmosphere and elevated local cuisine make it feel special without being overly stuffy. I highly suggest the Semolina Gnocchi (with cider-braised oxtail ragu). Their Cast Iron Focaccia and Smoked Beets are both delish as well.
Sunday: Fly Fishing, Breakfast, and Cheese Tasting
Early Farmers’ Market Breakfast and Fly Fishing
Start your last day in Woodstock with a quick stop at the Woodstock Farmers’ Market. (I mean it when I say quick; you have to be somewhere at 8 a.m.!) Somewhere between the grocery store and the farmers market, the brick-and-mortar local highlight has been serving Woodstock for 30 years, and it is THE place to shop for fall produce. Of course, you’re staying in a hotel, so produce might not be top of mind, but I still think it’s a valuable stop on your trip to witness local life. Plus, their grab-and-go menu is top-notch. Grab a breakfast sandwich on a Portuguese muffin before you head out on a fly-fishing adventure.
Fall is the best time for fly fishing in Vermont. Not just because that’s when the fish are more actively feeding (storing up for winter), but also because the scenery is just unbeatable. Imagine standing knee-deep in the crisp, cool Ottauquechee River surrounded by blue skies and the reds and golds of autumn. You can rent gear or book a half-day tour with Woodstock Inn’s Orvis-Endorsed Fly Fishing Excursion Program (I suggest a tour). Programs run from 8 a.m. to noon and take participants to the main river or a connecting spring, where they learn the basics of the sport. When I went, my guide (I wish I remembered his name) was incredibly knowledgeable. I had never fly-fished, and it was a challenge, but I found some success in the end!
Local Lunch and Afternoon Cheese Tasting
After all that wading and casting, you’ll be hungry. Tuck into a casual lunch at Farmer & the Bell. This sweet little cafe does great sandwiches and, if you’re in the mood, these out-of-this-world cruller donuts, made fresh daily. My go-to is the Avocado Supreme Sandwich with a sweet side of Maple Donut. Save some room, though; you’re going cheese tasting next.
Saving one of the best for (almost) last, get yourself over to Sugarbush Farm. This 550-acre, family-owned and run farm just outside of town has been pumping out cheese, maple syrup, jams, mustard, spreads, and more for more than 70 years, and it offers free entrance to all. Here, you can sample cheeses and maple syrup made on site and take a self-guided tour to learn how the farm does it all. Be sure to take home a block of their award-winning smoked cheese!
Farm-to-Table Burgers, Cinema, and Stars
We’re keeping it casual tonight at Worthy Kitchen. This relaxed order-at-the-counter joint is all about locally-sourced Vermont comfort food with a menu full of burgers, sandwiches, and dressed-up French fries (the poutine is to die for). The extensive beer menu is ideal for craft beer lovers. I really love their OG fried chicken sandwich and their pretzel bites with beer cheese.
After dinner, take a quick drive (or a 25-minute walk) to Pentangle Arts. This community hub puts on live performances and thoughtfully chosen film screenings throughout the month. Check their calendar beforehand to see what’s on. If a film doesn’t suit your fancy, consider a quiet walk through Woodstock’s adorable downtown, making sure to gaze up at the stars as you go. In the mood for a nightcap? Au Comptoir is serving up some stellar craft cocktails in a chic atmosphere.
Conclusion
And there it is! Your perfect autumn long weekend in Woodstock. It’s chock-full of fall colors, outdoor adventures, and culinary exploration with a hint of sophistication. A perfect combination if you ask me. I hope that you enjoy your time in one of the country’s prettiest small towns and bring home lots of fresh maple syrup and aged Vermont cheeses.
