From the Steamship wharf to the Lagoon Pond drawbridge, decades old, family-owned businesses line the Vineyard Haven waterfront. Among them are the Black Dog Tavern and the Black Dog Tall Ships, wooden boat builders Gannon and Benjamin, the Vineyard Haven Marina, the Martha's Vineyard Shipyard, and R.M. Packer Company.

The waterfront architecture is haphazard, but that is perhaps Vineyard Haven's charm — not quaint, per se, but certainly unique, plus it's rare for any town today to look much the same as it did 50 years ago.