There’s a great driving loop that circles Brattleboro and takes you through some “Real Vermont” country.
Here’s a map.
1. Start at Main & Canal, by the Food Co-op. Go through Malfunction Jct. and head south down 142 , along the river towards Vernon.
2. After about a mile +/- go right on Broad Brook Rd (Twisty road) to Rt. 5 in Algiers (Guilford).
3. Go right on 5 & quick left on Guilford Center Rd. for about 2 ½ miles. (This is past Fitch Road on the right and Clark Drive on the Left.) Look for some sand piles on the right (Highway Dept.). This is Guilford (Center).
4. Turn right, just beyond piles onto School Rd. Look for Town Office sign. (You will pass the Town Offices and Guilford School on right.) School Rd. becomes Bennett Rd.
5. About ½ mile later, Bennett intersects Bonneyvale Rd. (“T”-intersection). Turn left on Bonneyvale. This is the best part, as it is farmland – what Vermont used to look like. Bonneyvale twists and turns. Be careful at junctions so you stay on it. In about 6 miles you’ll be back in Brattleboro on Western Ave.
6. Turn right on Western to return to town. All told, it’s about 15 miles.
You can also do it backwards, but I know this way better.