My First Bike Overnight in Vermont

I kept it simple and rode from my home in Brattleboro to a B&B in Chester, Vermont. Oh, and it happened on Bike Travel Weekend!

Bicycle Adventurers? A solo trip, so just me 

When: I did this trip in early June, but any time in the spring, summer, or fall would be great. Remember, traffic can be heavy during fall foliage season, especially on the weekends.

Accommodations: Chester House Inn, Chester, Vermont

Distance: 70 miles in two days — I ended up riding 34 miles the first day and 36 on the second.

Bonus tip for this adventure? With mostly quiet but hilly roads, be prepared for some climbing! On the ride home, enjoy lots of gravel and the beautiful Vermont scenery, of course! Another tip: cell service in this area is spotty at best, so make sure you're prepared.

Day One

Spring in Vermont had been cool and rainy, but this trip started dry and sunny for a change. After a last minute check of my panniers to make sure I had everything, I headed on out. The route north out of Brattleboro is on Route 30, which winds its way along the West River. This section of Route 30 is great to ride with a fairly level road and nice wide shoulders. On a Thursday morning, traffic was light. 

The first stop of interest is the Dummerston Covered Bridge. It's a great place to pause for a few minutes and watch the river roll by. Continuing north on Route 30, I started to hit a few hills. Approaching Newfane, Route 30 narrows and the shoulders disappear, so care is needed through this section. A quick stop in Newfane allows you to enjoy the beautiful common with it's fountain, Windham County Courthouse, Congregational Church, and Union Hall. It's claimed to be the most photographed village commons in all of New England. 

My ride continued north on Route 30, still winding with narrow shoulders. After an initial rise out of Newfane, there's a nice downhill stretch before climbing a bit to get into Townshend. If you're feeling the need for a snack at this point, check out the Harmonyville store as you're entering Townshend. It's a typical Vermont country store and deli, with a great supply of freshly baked cookies. 

In Townshend, I headed out on Route 35 and after a few miles turned onto Grafton Road. There's a killer two-mile hlll right as you turn onto Grafton Road, but once you've climbed it, it's a pleasant five- or six-mile downhill journey into the pretty town of Grafton. I was about 27 miles into my trip, and it was getting close to lunchtime. The Grafton Market has some great sandwiches, as well as some nice outdoor seating. 

Realizing I only had about seven miles to go, I lingered a bit over lunch, watching the local crowd come in for lunch. After about 45 minutes, I motivated myself to move on. The route from here jumps back onto Vermont 35 and starts out with yet another killer hill out of Grafton. This one is short, however, and once over the top, it's a comfortable glide all the way to the town of Chester. Note that there are no shoulders at all, but fortunately, traffic is very light and the drivers that do go by tend to be very courteous to cyclists. 

Arriving in Chester around 1:30, I decided it was just a bit too early to check in to my B&B, so I spent some time cruising the main street and sitting on the common and watching traffic go by. After a bit, I wandered over to the Chester House Inn, right on Main Street and was greeted by Bob. He showed me my room and gave me some great advice about local options for dinner. I ended up choosing The Free Range, a close walk from the Inn, serving great local food and beer.

Day Two

I started out with an excellent breakfast at the Chester House Inn. There's nothing like blueberry pancakes with fresh Vermont maple syrup, sausage, fruit, and of course coffee, to get you prepared for another day on the road. The weather forecast for the day called for rain starting in the early afternoon, so I decided to book it for home. After bidding farewell to my innkeepers, I rolled my bike out of their barn and hit the road. 

The route I chose for the return trip was much more rural then the first day with more than half the miles on gravel. There's very little in the way of stops for snacks or lunch, so I made sure to carry some energy bars for the trip. On the plus side, I was expecting some beautiful Vermont scenery. I started by heading south on VT-103, and after a few miles turned off onto old Route 103, and then Cambridgeport Road, which is gravel. Over the next five miles, I experienced some gentle climbs and nice downhills riding past old farms and pastures and a few new homes. Not a car was to be seen until I arrived in the tiny village of Cambridgeport. There's a small market in Cambridgeport, if you're in need of some snacks. 

From Cambridgeport, I rode back on pavement for a few miles, but then jumped onto Brookline Road with yet more gravel. A few miles in, I saw a road sign that said, “Road Grading Ahead.” Uh-oh. The road got bumpy and before long, I caught up to a town truck pulling a rake, moving along at about five MPH. I managed to scoot on by and the road got just slightly less bumpy. After a few more miles, I caught up to the road grader. He took up the whole road and moved even slower than the truck. I had to follow him for two miles before he reached the town line, and pulled off the road with a wave. 

Once clear, the road smoothed out, and I enjoyed a fast gravel road ride that took me by some ponds that have crept right up to the edge of the road because of our recent rains. Going through the town of Brookline, I stopped at the empty Town Office parking lot, and sat on the lawn enjoying a snack and some water. Across the road sits the Brookline Round Schoolhouse, a wonderful old brick structure. 

From here, it's a final push along River Road, past a pretty horse farm, and then back onto Route 30 for the final few miles back into Brattleboro.

Your favorite local bike shop? Well, I have two: West Hill Shop in Putney and Burrows Sports in Brattleboro (Burrows Sports Facebook page).


HOW ABOUT YOU? Inspire others by submitting your own bike overnight adventure!

1 response so far ↓

Paul - Jan 5, 2018 at 8:12 AM

Great trip description:
1. Details about the roads (hills, decents, shoulders, traffic)
2. Enticement (relaxing on the greens, food, beer)
3. Excitement/adventure (following the grader)

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