Take a trip up Historic Route 7, the old picturesque two-lane highway that runs from Bennington through Shaftesbury, Arlington, and Sunderland and on to Manchester. Just north of Shaftesbury is a little unpainted barn on the left hand side of the road that acts as the workshop for David and Patty Herzfeld, proprietors of Bottum Hill Studio. David is a talented artist, equally at home in making beautiful hand-crafted custom furniture as he is in drawing and painting. Patty specialises in pottery, and both are becoming increasingly popular amongst locals and visitors alike. Continuing north, you will come to Arlington and its attractive village center. You may find an old book sale going on at the local library, a bake sale at the local church, or a student car wash at the local gas station. This is very much small town America and a pleasant place to stretch your legs.
North of Arlington, keep your eyes peeled for Christmas Days, a specialty shop run by Andrew and Linda McKeever. I was never one for Christmas stores in the summer, but those seasoned shoppers and credit card addicts that I know swear by this shop.
You are now entering Sunderland territory. Look for the little gift shop across the highway from the basket store. This shop carries without a doubt the creamiest, richest home-made fudge you will find anywhere in Vermont. And what a variety. You can't go wrong with the chocolate walnut (the cure for my chocolate cravings), but try some of their specials as well.
If you are looking for something as rich but a bit cooler, just up the road is Wilcox Dairy, a supplier of dairy goods to the local southern Vermont community. A dirt road takes you to the dairy itself, currently rebuilding after a fire devastated the old wooden barn. It also takes you to a little wooden hut which sells fresh, homemade ice cream. Sitting on a bench in a dairy farm off the main highway, with the sun in your face, country air in your lungs, and a praline and cream cone in your hand--it can't get better than this.
Just past the dairy is the family-owned Equinox Valley Nursery. Even if you're not in the market for plants, this is a fun, friendly stop, especially during October, when the nursery goes all out with a fall and Halloween theme that attracts thousands of families from throughout the Northeast.
Manchester itself is home to dozens of exclusive factory outlet stores eager to relieve you of your cash. Save it for Al Ducci's Italian Pantry on Elm Street. Al has a egg plant parmesan that would make even die-hard Italian-Americans weep. It's a bustling place, especially around the lunch hour, and most of the good stuff, including their breads, is gone by mid-afternoon, so get there as early as you can.