The patriarch of Cape Cod towns, Chatham has a genteel reserve that is evident along its shady Main St: the shops are upscale and the lodgings tastefully swank. That said, there's something for everyone here – families flock to town for seal-watching and birders migrate to the wildlife refuge. And then there are all those beaches. Sitting at the 'elbow' of the Cape, Chatham has an amazing 60 miles of shoreline along the ocean, the sound and countless coves and inlets.
MA 28 leads right to Main St, where the lion's share of shops and restaurants are lined up. Chatham is a town made for strolling. You'll find free parking along Main St and in the parking lot behind the Chatham Squire restaurant (but you'll have to fight for a space in summer).