- Watch a sunset with a picnic at Menemsha beach
- Make a friend with a pass to Lucy Vincent Beach
- Surf the waves at Squibnocket
- Grab a slice of pizza and eat in on the porch of the Chilmark General Store
- Take a hike on any of Chilmark’s gorgeous walking trails
- Catch a performance at Pathways Arts, or the Chilmark Community Center
- Run the famous Chilmark Road Race, a grueling, mostly-uphill 5k
- Shop the antique and thrift shops surrounding Menemsha harbor
- Take your bike from Chilmark to Aquinnah on the Menemsha bike ferry
