Since I live in Bennington, I’ve become an expert at day trips well within a half day’s drive from Bennington. Located in the Southwest corner of Vermont, Bennington is close to Williamstown, MA, as well as the Stratton ski slopes and it’s only about 45 miles from Albany NY and its international airport.
Day trips really depend on what type of day you are looking for. The first easy trip is more of an upscale type of day, if you like dining and shopping, you should head up to Manchester and Dorset, Vermont. The easiest thing to do is to head straight up Scenic Route 7A. (or the Shires of Vermont byway) You can also take direct Route 7 but it’s not as pretty.
Your first stop can be in Shaftsbury, VT, home of the lovely Robert Frost house. The home where Frost wrote “Stopping by Woods on a Snowy Evening” (which ironically was written on a hot June morning), it’s a small museum on a compact but picturesque lot, perfect for photos. Also located in Shaftsbury is the Market Wagon, a Mennonite-owned general store that is a local fave, everyone in Bennington shops at the Market Wagon and it’s a great place to pick up pancake mix, spices, and Vermont goodies without the tourist trap kind of vibe.
Halfway to Manchester is Arlington, Vermont. Vermont’s first capital, Arlington is a country town, but a few of my local food faves are there, including the Arlington Dairy Bar (a true old-fashioned Dairy Bar, try the clam strips or lobster roll and an ice cream, of course!) and the Chocolatorium (there’s also one in Bennington) and my personal must-stop, the Sugar Shack. The Sugar Shack has a small Norman Rockwell exhibit and has the best maple creemees and cider donut sandwiches, and I love the owner Kimberly! If you come during sugaring season they do have a real live sugar shack so be sure to pick up some of their syrup and other VT-themed goodies!
Vastly different from the rural Arlington vibe is the town of Manchester. Manchester is a very upscale, retail-based town, it has an outlet shopping center which is its main focus (in a New England way) and the Orvis flagship store is a must-stop. Manchester is home to the Equinox Inn, a Vermont favorite, and there are tons of restaurants and dining options.
Manchester is not my absolute favorite but it’s very cosmopolitan. You can use their website to plan your dining and shopping options.
Next, you can head northwest up VT 30 to Dorset, Vermont. Dorset is much smaller but has the same pristine vibe as Manchester. Dorset boasts the Dorset Inn and Dorset Green, both of which are charming and wonderful photo ops. The Dorset Inn is some of the finest dining in Vermont.
You can also head over to the tiny town of East Dorset. If you do this, you can continue up Route 7 through Danby and Mt. Tabor, and the mini golf course in Mt. Tabor has great creemees and snacks! That’s about it up Route 7 unless you need to go to Walmart in Rutland, lol!
Once you’re in Dorset, if you enjoy farmland and lovely rolling hills with peeks of the Adironacks (peeks and peaks!) you can continue heading up Route 30. Your first stop can be Merck Forest if you’re into hiking and farms. Route 30 is known as the Stone Valley Byway and it winds through the gorgeous Mettowee Valley. This is farmland similar to the midwest, there’s not a lot to do here but it is verdant, rolling farmland. You can drive up to Wells and stop at the Wells Country Store for a snack. There is also beautiful Lake St. Catherine up here. You can see some of my photos from Pawlet and Poultney here. If you’re looking for dinner in a classic rustic setting, The Barn restaurant in Pawlet is a great choice.
A different day trip is to head east. So you would take Route 7 to Manchester, then Route 30 WEST through Peru (home to Bromley Ski Mountain) and Londonderry. Hang a right on Rte. 11 over to Rte 121. This is a dirt road, not always passable in winter but fine in summer, and this will take you over to Grafton. The town of Grafton boasts the Grafton Inn and is truly one of the most picturesque towns in Vermont. There is NO cell service in this town, but don’t let that stop you. It is so sweet and has the most beautiful vistas right in the town. Rte. 121 in and of itself has some of the prettiest farms and houses in all of Vermont in my opinion, and is home to secret celebrities (I think!) who just want to get away from it all.
You also don’t want to miss Weston. Weston is home to the Vermont Country Store which is now open again, and another one of the most charming Vermont small towns. It has a lovely town green and some museums, as well as the Weston Playhouse which is world-famous for theatre. So once you’ve hit Grafton, you could circle back and when you get to Londonderry, and go north on Route 100, or the Scenic Route 100 Byway. This will take you right through Weston (coming in from the south, be sure to take a left at the town green and head up the hill for some lovely homes on waterfalls there).
Everyone who comes to Vermont wants to go to Woodstock, as well they should. Home to the world-famous Woodstock Inn, Woodstock is the epitome of small town New England. It is lovely with a town green and covered bridges, plenty of dining options and a charming main street. The drive would be from Weston to head up Route 100 through Ludlow which has Okemo Ski Mountain, which is huge and quite spectacular in winter (Ludlow is cute too). In Plymouth, bear right on 100A which will take you up to Bridgewater Corners, which has a great brewpub, The Long Trail Brewing Company. Annnddd that’s about it, but there’s some great barns along the way. In Bridgewater, hop on Route 4 which takes you directly into Woodstock. You can continue on through Woodstock over to Queechee which boasts the beautiful Queechee Gorge and the famous Simon Pearce glass factory and restaurant. An elegant spot for a leisurely lunch, you don’t need to continue on the White River Junction (and God forbid New Hampshire lol!) so this is a great turnaround spot.
You can wend your way back down from Woodstock on the eastern side of the state down to Wilmington, I don’t think it’s as pretty of a drive as going back the way you came, but you can. Alternately, a fresh day trip would be to take the Molly Stark Byway, or Route 9, from Bennington over to Wilmington. This is a great route for fall, as it is absolute prime leaf-peeping territory. You’ll head east out of Bennington and cross through Woodford, where Prospect Mountain Nordic Ski area is located. Also Hogback Mountain Lookout is a classic tourist spot, you can see for miles and it is absolutely jammed in fall. You’ll pass through the town of Wilmington which in my opinion is not as charming as Grafton or Weston but it’s more cosmopolitan, and people love it. There are plenty of restaurants (like the Village Roost Cafe, pictured above, which also has a great Ski the East popup shop) and some cute antique shops. It’s a few miles down the road from Mt. Snow which is also not my favorite ski mountain and I just don’t think it’s as pretty up there as Okemo or Stratton, but people seem to like it. From Wilmington you could conceivably continue on north to Woodstock and go up the eastern side of the state. Once again, Southeast Vermont does not have as high of elevations and just isn’t as pretty in my opinion. Brattleboro is meh to me, it lacks that Vermont vibe and sadly has a terrible, terrible heroin problem right now, its proximity to Mass and NH sort of give it that gritty, less Vermontly vibe, but there is a Dunkin there if you need it. I would give it a pass, you’re not missing a lot if you’re into scenic photography. But the Molly Stark Byway through Wilmington and Hogback is an absolute do not miss for fall (just be prepared for crowds).
A few other towns that are super photogenic and scenic though more out of the way are Jamaica and Chester. Jamaica is tiny but it has the most spectacular river and waterfall right in town, just breathtaking. The whole town was washed out in Hurricane Irene and in true Vermont fashion, they rebuilt it. There’s a little coffee shop there you can get a coffee and pastry (and really good homemade mac and cheese come to think of it!). Chester has a super cute main street, also one of those classic New England towns, it’s just sort of remote and not on any main byways so it’s kind of out of the way, but it really is cute in that Victorian, New England way. You can work Jamaica and Chester into your drive but you have to make a point to do it.
Since I live in Bennington, I would never do all of these trips in one day, we can make a whole day out of just driving up Chester Mountain, but if you’re trying to get the most bang for your buck, you can also check out Vermont Tourism’s Byways of Vermont page, this details every byway in Vermont.
In summary: Road Trip Ideas:
Shires of Vermont Byway: Take Route 7A from Bennington to Dorset, through Shaftsbury, Arlington and Manchester. Once in Dorset, if you are looking for farmland, continue on up Route 30 (Stone Valley Byway) through the Mettowee Valley.
Highlights: Manchester (upscale shopping and dining), Dorset (The Dorset Inn and town green), The Barn restaurant in Pawlet (rustic dinner dining)
Scenic Route 100 Byway: Take Route 7 to Peru/Londonderry. This will take you through Shaftsbury, Arlington and Manchester. Take Route 30 to Route 11. At the old house (an instagram classic)/Farmer’s Market parking lot in Londonderry turn left onto Route 100. This will take you through Weston, Ludlow and Okemo Mountain. You can follow Route 100 (or 100A) to Bridgewater and hop on Route 4 to Woodstock and go on to Queechee if you choose. This is a long day.
Highlights: Manchester (upscale shopping and dining), Weston (classic town, Vermont Country Store), Ludlow (ski town with tavern-style dining), Woodstock (classic upscale New England shopping and dining, covered bridges, Woodstock Inn), Queechee (Queechee Gorge and Simon Pearce)
Optional: Detour to Grafton (classic New England town, Grafton Inn, Grafton Trails outdoor center)
Molly Stark Byway (Route 9): Take Route 9 from Bennington to Wilmington/Hogback Lookout. You can continue on to Brattleboro and take Highway 91 up to Queechee/Woodstock or you could wind your way up to Woodstock on back roads and travel through Grafton and Chester.
Highlights: Prospect Mountain Nordic Skiing, Wilmington (classic New England town with Dot’s Diner), Mount Snow ski mountain, spectacular leaves in fall, not as pretty in summer.
If you’re looking for a longer trip and to get up north, you can check out Back Road Ramblers wonderful post on 5 Days on Route 100!
You can view all of these Byways in more detail by going to Vermont Tourism’s Byways of Vermont page.