After crossing the Vermont border from Massachusetts, one of the things I love about Vermont is that almost all the main roads travel through picturesque towns that are just calling for a pit stop. Route 9 runs parallel to the Massachusetts border from Brattleboro to Bennington. This road is also called the Molly Stark Trail, named after the wife of a Revolutionary War General. 

Brattleboro sits along the hillside of the Connecticut river separating Vermont from New Hampshire. The impressive Greek Revival facades along Main street mix with the colorful graffiti on the side streets to create a down to earth town that embraces its past and honors its locals. Many of the stores in the downtown area do the same: vintage shops like Boomerang, Twice Upon a Time, and Turn it Up find new homes for older wares; artisan galleries like Gallery in the Woods and Harmony Collective Artist Gallery showcase Vermont artists. Since I don’t have a Co-Op grocery store near me, I also make sure to shop at the Brattleboro Coop to stock up on loose spices, grains, and the like before heading home. 

Route 9 drives up and down Hogback Mountain (elevation 2,400 ft), which always makes my ears pop and makes me a little dizzy. Thus, the viewing area and the Hogback Mountain Country Store  in Marlboro was a good place to take a break and let my body adjust to the elevation gain. The large wooden platform offers a 100 mile view looking out to both New Hampshire and Massachusetts. There is a Brewpub across the street and a Distillery at the end of the parking area that would work as nice rest stops, but because I still had a fair amount of driving to do, I wasn’t ready for a long break yet. I’ll have to check them out on my next trip. 

One of my main stops on this trip was in Wilmington. This small town has everything I look for: local shops, coffee shops and small eateries, walkability, and views. Some notable stops in the town were the church that has been turned into the Arthouse Studio Gallery and Lounge, the comfy sitting area in the back of the Village Roost, and rustic 1836 Country Store. The North Branch of the Deerfield River runs through the center of town, and a few of the restaurants and bars have small decks to enjoy the view. Reardon’s Crossing at the western edge of the downtown area provides a nice view of the river as well. The river, however, hasn’t always been good to the city of Wilmington as noted in the flood lines drawn along a building at the main intersection. 

Bennington is known for its Revolutionary War history and many of the buildings are still standing from this time period. The downtown area currently has a few breweries, shops, and eateries; but it definitely has the potential to be even better.  There are a few places outside of downtown Bennington to make sure to check out.

First is the Bennington Battle Memorial. Set on a hill, this Washington monument look-a-like is visible from surrounding towns as well. The memorial honors those who fought in the pivotal Battle of Bennington in 1777. While the monument was open for tours, I arrived right after a large tour bus; so I decided not to wait around for my chance to see the views from the top. I climbed several mountains during my trip, so I can imagine the beautiful view of the surrounding mountains and valleys that one would have from the top of the monument. 

No trip to Vermont would be complete without at least one covered bridge, and North Bennington offers a set of three quintessential red covered bridges (Paper Mill Village, Silk Covered and Burt Henry). Unlike some covered bridges that have become only for photos, all three of these bridges are still drivable and offer small parking areas to pull off and take pictures. 

During the summer months (June-November), the North Bennington Outdoor Sculpture Show (NBOSS) takes over the village of North Bennington.  The show features more than 70 sculptures created by more than 40 local artists. I parked at the train depot (which was a cool building in itself) and explored much of the exhibition from there. The sculptures ranged in material and professional quality, but all were colorful and unique.

I traveled to this area in the autumn so was constantly on the lookout for picturesque farm and mountain walks where I could take in the beautiful fall foliage. This search brought me to The Mile-Around-Woods.  Donated to a The Fund for North Bennington in 1994 by the McCullough-Scott family, The Mile-Around-Woods offers walks along carriage trails from just after the Civil War and trails through former dairy fields. Here I greeted the resident horses, wandered the rolling hills, and navigated the shaded forest area. The walk was peaceful, picturesque, and perfect for what I was looking for.