How to experience fall in Vermont, all on one road

I’ve always loved road trips and have taken them around the world, from Australia’s Great Ocean Road to South Africa’s Garden Route. But one of my absolute favorites is much closer to home: Route 100 in Vermont, which begins just two hours from my hometown of Boston. Unofficially known as the “Skier’s Highway,” it traverses the eastern edge of the Green Mountains where many of the region’s best ski resorts are found. And while I love to drive this route any time of year, fall tops my list. The foliage is brilliant, the cool (but still sunny) days are perfect, and the vibes come nightfall are at their absolute coziest.

Each time I visit Route 100, I find something I’ve never noticed before, whether it’s a historic building, a new-to-me antique shop, or a fresh scenic view. And while you could drive the whole 216-mile-long route in a single day, I like to take my time, breaking it up over a leisurely weekend. Drive for half an hour, stop for a hike here, drive a little further, stop for a snack there. Your itinerary can be as quick, slow, outdoorsy, or food-focused as you want.

The highway connects a number of the state’s most charming small towns, so while the scenery definitely includes mountain views and swathes of protected forest, it also means that gas stations, snacks, and things to do are never (much) more than a few minutes away. For that reason, you can leap into a Route 100 road trip with little-to-no advanced planning. Here, a few of my favorite spots to save before your next fall drive.

There’s really no right or wrong place to stay along Route 100. Where you decide to rest for the night all depends on how much ground you’d like to cover in a single day. The owner-operated Hermitage Inn in West Dover is surrounded by gorgeous grounds where you can take in the foliage views from the comfort of your room. Further north, the Pitcher Inn, a Relais & Chateaux property, also offers well-appointed rooms with an enviable dining room. For younger travelers or those getting around in a group, Field Guide Lodge in Stowe offers plenty of social spaces, a hot tub, and a bar frequented by visitors and locals alike.

I love New England for its general stores, but Vermont does them especially well. This is where you’ll find souvenirs, maple syrup, sandwiches, and more all in one place. They are very often the most popular place in town for locals to congregate over a morning coffee and exchange gossip. For that reason, I always try to pencil in some leisure time for people-watching at a general store.

The alpha and omega is the Vermont Country Store in Weston, the original location that inspired an enormous catalog business that now sells everything from flannel nightgowns to locally made candy. And for a true insider favorite, check out the adorable Warren Store—the pulled-pork sandwich with sharp cheddar cheese and smoky barbecue sauce is unreal.

Vermont is a treasure trove of artisanal makers and bakers so there is a plethora of snacks for hiking, snacks for the car, and snacks to bring home. On a crisp fall day, there’s nothing better than a warm cinnamon roll from Sticky Fingers Bakery in Dover. Grandma Miller’s in South Londonderry is also a great place to pick up fresh or frozen pies; they’re famous for their apple pie (gooey, just tart enough, with a flakey crust) and their chicken pot pie. And no trip to Vermont would be complete without picking up some maple syrup (the state regulates the viscosity of what can be billed as “maple syrup,” meaning you won’t find a bad bottle). Green Mountain Sugar House has syrup, maple candies, and quintessential “maple creemee”: the state's famous soft-serve ice cream.

But Vermont’s snacks are not just relegated to the traditional variety. Up in Waterbury, you’ll find Vermont Artisan Coffee & Tea—a hip-feeling coffee roaster that pulls some of the meanest espresso you’ll find anywhere, as well as the Ben & Jerry’s headquarters, which offers both factory tours and a delightful Scoop Shop.

Vermont is especially famous for its sharp cheddar, and Cabot Creamery, which operates a great Farmers’ Store in Waterbury on Route 100, has won international awards for its offerings. But one of my favorite road-trip resources is the Vermont Cheese Council website, which has a “cheese trail” map. Check out the adorable shop at Plymouth Artisan Cheese in Plymouth, or consider joining one of the cheesemaking classes at Three Shepherds Farm in Warren.

There are tons of trails to hike in Vermont. From Route 100, there aren’t any treacherous spots to be overly cautious about, so if you see signs for trails on the side of the road, follow them. Two off-the-radar favorites include the Kingsbury Bridge Greenway and Farm Path, a relatively flat 2.5-mile walking trail in Warren, and the Coolidge State Park trails network further south in Plymouth. Head for either of those easy hikes and you’ll be surrounded by the stunning autumnal beauty of Vermont’s foliage.