Things To Do
Food & Drink - Breakfast
Salisbury, CT - There are some great breakfast options at Provisions (directly next to the White Hart hotel). Sweet Williams Coffee Shop & Bakery is also perfect if you’re in the mood for pastries. All of this is located in the downtown area, which is very walkable and also has lots of mom and pop stores if you’re in the shopping mood! Sharon, CT - J.P. Gifford’s is great for breakfast sandwiches/bagels or lunch salads, wraps, and more. Coffee is great here too! If you’re staying at the Sharon Country Inn also worth considering a cute French café called Le Gamin. Millerton, NY - Irving Coffee's hometown! And for tea fans, check out Harney & Sons.
Food & Drink - Lunch
Wassaic, NY - The Lantern Inn is a bar/restaurant that serves great bar food i.e wings, wood-fired pizza, etc. Has a big upstate vibe as well as a super spacious outdoor portion with tons of benches and fire pits – a great place to have a fall hang! Lakeville, CT - The Black Rabbit is a small bar with TVs and very good lunch options. Perfect for those looking to set up and watch a college football game (or 5).
Outdoor Activities
Millerton, NY - The Harlem Valley Rail Trail travels right through the downtown area (another super walkable town with local stores) and is 26 miles of scenic pathway. Perfect for a nature walk, run, or even bike ride! Also very easy access if you’re staying at the Millerton Inn. Millerton, NY - The Farm Store at Willowbrook is a large property with events every weekend in the fall. If you’re in the mood for pumpkin patches, farmer’s markets, or even a corn maze then this place is definitely worth checking out.
Golf
Salisbury, CT - Hotchkiss School Golf Course Litchfield, CT – Stony Brook Golf Club