The first day of fall has come upon us, and we are in full autumnal force here in Vermont. A change in leaves transforms the lush forest we’ve become so accustomed to over the summer months. New England now explodes with fiery reds, bright oranges, and brilliant yellows, mainly thanks to our glorious sugar maples. Their leaves gently fall onto our trails and roads, and speckle the landscape with magnificent color – a grand celebration of the crisp weather swooping into our Green Mountains. At this time of year, we encourage you to pull off the main roads and explore! Check out those roadside waterfalls and hidden notches. Travel over the state’s famous covered bridges and through its rolling hills. Take in the sights on your way to a quaint country store or awesome brewery. Let us help in mapping your journey … we have five route suggestions, along with various points of interest below. Now go out and experience all that Vermont has to offer!
North Loop for the country store enthusiast
| map it here | 55.6 miles
Take Route 12 North from Woodstock, traveling past Billings Farm & Museum and the Marsh Billings National Park. Continue through Barnard. We suggest peeking into the Barnard General Store to pick up a snack for the road! Drive past Silver Lake to the intersection of Routes 12 and 107 (Rood State Park). Take Route 107 West toward the Green Mountains, through Gaysville to the intersection of Routes 107 and 100. Turn onto Route 100 South through Pittsfield. Be sure to visit Pittsfield’s Original General Store for a quality sandwich and killer fries. They also have gifts and goods that kick up the caliber of Vermont country stores. As you drive toward Killington, the Green Mountain National Forest is on your right (to the west). At the junction of Routes 100 and 4, turn east on Route 4 and follow for 20 miles. Along the way, take a short side trip to Killington Mountain or make a stop at Long Trail Brewery in Bridgewater Corners or The Bridgewater Corners Country Store before returning to the inn or the village of Woodstock.
Points of interest: snack at Barnard General Store, lunch and gifts from Pittsfield’s Original General Store, drinks at Long Trail Brewing Company
South Loop for the artisan collector
| map it here | 53.6 miles
Take Route 4 West from Woodstock. Stop into Farmhouse Pottery for an up-close look at the potters throwing the very pieces displayed in their beautiful shop. A little further down, in Bridgewater, we suggest also peeking into Shackleton Thomas for fine handmade furniture and pottery. Continue on Route 4 and turn left onto Route 100A. You will pass the Calvin Coolidge birthplace, as well as Plymouth Artisan Cheese. This is the perfect spot to tour Plymouth Cheese’s museum, taste some delicious cheddar, and maybe even catch some sheep sheering! Continue on to the intersection with Route 100 and turn left onto 100 South through Tyson, past Okemo Mountain Ski Resort, and into the town of Ludlow. We highly suggest Homestyle Hostel or Downtown Grocery if your stomach is hankering for dinner or drinks. In Ludlow, you will want to turn right onto Route 131 East, towards Proctorsville. Take 131 East through Proctorsville, Cavendish (former home to Alexander Solzenitchen), to Downers Corners. At the junction of Routes 131 and 106, turn left on Route 106 North. Travel north through Felchville, Reading, Hammondsville, and South Woodstock. Continue north five miles to return to the village of Woodstock.
Points of interest: shop in Farmhouse Pottery and Shackleton Thomas, tour and taste at Plymouth Artisan Cheese / Calvin Coolidge Homestead, dinner at Homestyle Hostel or The Downtown Grocery
Northern Exposure for the beer advocate
| map it here | 217 miles
Vermont in a Day (or two) “North” – Take Route 12 North from Woodstock, continue through Barnard (stop at the Barnard General Store for a look and a snack for the road), Bethel, Randolph, Northfield, to Montpelier (or follow signs to I-89 at varying points for a faster, less scenic option). Spend time visiting Vermont’s capital city (the smallest state capital in the US). Shop, indulge at the restaurants operated by the New England Culinary Institute, and tour the State House. A short drive outside town takes you to the Morse Farm Sugarworks. Return to I-89 North and travel to exit 10 for Waterbury. Depending on the time of day, we suggest grabbing a bite or drink at Prohibition Pig (for lunch/dinner) or Hen of the Wood in Waterbury (for dinner). Don’t forget to grab a sweet treat while touring the Ben & Jerry’s Ice Cream Factory too! Looking to stay a bit longer in the area? Check out Stowe. We consider Doc Ponds (also owned by Eric Warnstedt and William McNeil of Hen of the Wood) and Alchemist Brewery to be the highlights. Don’t fear the lines – it’s worth the wait for Heady Topper! Continue north on I-89 to the city of Burlington. Take in a walk or cruise along Lake Champlain, and be sure to shop and nosh on Church Street. However, we think you should save room for some brewskis at Burlington Beer Company, as well as a foodie-acclaimed dinner at Misery Loves Company (just outside Burlington in Winooski). Once you’re stuffed, head south from Burlington on Route 7. Views and attractions galore await you on Route 7. To the right, behold a picturesque view of the Adirondack Mountains across the water. Stops can include Magic Hat Brewery, Shelburne Museum, Vermont Teddy Bear Company, and Fiddlehead Brewing Company. Route 7 South continues through the beautiful Vermont towns of Middlebury (home to Middlebury College) and Brandon (a town with 243 buildings on the National Register of Historic Places). Once you hit Middlebury, you should check out Drop-In Brewing Company and Stonecutter Spirits as well. Just south of Middlebury, take Route 125 East. Alternatively, you can go further south to Brandon and take Route 73 East. Continue through the Green Mountains and turn right on Route 100 to Route 4 East toward Woodstock.
Points of interest: snack at Barnard General Store, eat and drink at Hen of the Wood or Prohibition Pig, satisfy the sweet tooth in Ben & Jerry’s Factory, grab more grub at Doc Ponds Restaurant & Bar, grab coveted brews at Alchemist Brewery, sip at Burlington Beer Company, indulge at Misery Loves Company … continue to taste at Fiddlehead Brewing Company, Drop-In Brewing Company, and Stonecutter Spirits
Southern Wandering for the hungry foodie
| map it here | 128 miles
Vermont in a Day “South” – Take Route 4 West from Woodstock to 100A at Bridgewater Corners. Visit the Calvin Coolidge Homestead and Historic Site next to Plymouth Artisan Cheese. Continue south on 100A and turn left on Route 100 South toward Ludlow. Enjoy views of Echo Lake and Lake Rescue, and make a quick stop at the Green Mountain Sugar House or Okemo Mountain Resort. Continue through Ludlow on 100 South to the town of Weston. Here, you should carve out an hour or so to explore the impressive Vermont Country Store, chock full of classic candies, cozy flannels, cheese, jerky, and toys. Grab one of their tote shopping bags and go to town! Once you’ve gotten your shopping fix, drive south on Route 100. Hungry for lunch or dinner yet? Chloe & Wesley Genovart have two options to satisfy your needs: one casual gas-station-turned-burger-joint, Honeypie, and one fine dining farm-to-table restaurant, SoLo. Continue south on Route 100 and turn on Route 11/30 West to head toward Manchester Center (home of numerous outlet shopping centers and the flagship Orvis store and outlet) and Manchester’s Hildene (the summer estate of Robert Todd Lincoln). Two options to go back: (1) Take Route 7A North to Route 7 North (shadowed by the Green Mountain National Forest on your right) to Rutland. Turn east on Route 4 in Rutland and follow for 30 miles. Along the way, take a short side trip to Killington Mountain or make a stop at Long Trail Brewery in Bridgewater Corners before returning to the inn/village of Woodstock. (2) Return to Woodstock via Route 100 and stop by Homestyle Hostel or The Downtown Grocery for dinner or mind-blowing cocktails.
Points of interest: visit and taste at Plymouth Artisan Cheese, dine at SoLo Farm & Table or Honeypie, tour Hildene, shop at Orvis Flagship Store and Orvis Outlet Store
The Gap for the nature lover
| map it here | 132 miles
Take Route 4 West to Route 100 North near Killington. Enjoy the views as you wind your way through Pittsfield (stop at the Original General Store for a special “something for the road”). Continue to Route 73 West (the Brandon Gap). Cross the Green Mountain Forest to the historic town of Brandon, a town with over 200 buildings on the National Historic Register. Gourmet Provence Bakery will fill your need for a tasty bite or Cafe Provence for a lunch or afternoon bistro snack. Head north on Route 7 to the town of Middlebury, home of Middlebury College and a lovely downtown on a river with a waterfall. Retrace your trip briefly south of Middlebury onto Route 125 East to drive back over the Green Mt. National Forest once again. Stops can include the Robert Frost Interpretive Hiking Trail in Ripton and Texas Falls just a few miles further. Head south on Route 100, turn east on Route 4 and follow for 20 miles back to The Jackson House Inn. Along the way, take a short side trip to Killington Mountain or make a stop at Long Trail Brewery in Bridgewater Corners before returning to the inn.
Points of interest: snack at Pittsfield’s Original General Store and Gourmet Provence Bakery, walk the Robert Frost Trail, sip in Long Trail Brewing Company
