chester, ct

meant for this to be a stop-for-gas town on our way to a hike and we ended up staying the entire day and had to talk ourselves down from impulsively getting an airbnb to spend the night. this cutie little town has a walkable main street with boutique and antique shops, a bookstore, and several small food businesses.

rec within a rec: stop by little house brewing for a pint, free popcorn, and a game of hook and ring! even better if you time your visit to their bimonthly meat raffle (be still my midwest-raised heart). if you stop by the brewery around a mealtime, order otto pizza from across the street, they’ll either deliver it to your table (no fee) or call you when it’s ready for you to pop over and back!