Posted On: September 7th 2026, 12:47 am
Day 4 solo bike-about: Waitsfield to Woodstock. 63 miles and 4500 ft of climbing. This was a good learning day! Lesson no. 1 while i stand by my rule of not booking a hotel until the day of, it was maybe not the wisest choice when riding into fancy-pants Woodstock on Saturday of Labor Day weekend.😊 everything was booked online so I had to resort to the old walk-in trick. Fortunately, I landed in the coolest spot in town and got one of their last rooms! The Village Inn of Woodstock is hip in a very old-fashioned Victorian way and that’s not an oxymoron, and the Vic Tavern downstairs is definitely the coolest vibe for dinner. So lucky me!2: when you don’t have a place to stay, you waste a lot of time along the way Google searching what’s available. And stopping to charge your phone. (in my haste leaving Middlebury, I left my portable charger in the car whoops.) lesson #3 gravel is wayyyy more fun, but a lot slower but still my favorite. When I’m on the road I always feel like I’m just trying to get somewhere. When I’m on the gravel, I’m exploring . 4: stop at the local bike shop for route tips. I got more from my new friend Dylan at the Rochester bike shop than I could’ve gotten on any app. #5 always stop at the creamee window. 6. Woodstock is drowning in cuteness, maybe too much cuteness? 7. One pair of socks is not enough. 🍦💚🚲🩷
#bikepacking #vermont @villageinnofwoodstock