Downtown Chatham isn’t exactly convenient to the water, but that shouldn’t stop you from visiting this lovely town by boat. Set a course for Chatham Roads then head north towards Stage Harbor. At the truncated lighthouse to port, you have 2 options: continue north into Stage Harbor and grab a mooring or slip at Stage Harbor Marine, Oyster River Boat Yard or Chatham Yacht Basin, or bang a right and follow the winding channel east to Outermost Harbors, where you can rent a slip before strolling the mile or so into town.
The marinas in Stage Harbor (the better choice for boats 30’ and up) can arrange a lift to Main Street, but it’s more fun to take a dinghy or kayak up either the Oyster River or the Mitchell River. Both feature public landings—or at least a place to beach your boat or kayak—close to Main Street, where you’ll find all manner of shops, galleries, boutiques and restaurants. Enjoy dinner, a beverage and live music at the famous Chatham Squire Tavern or the Red Nun, or spend a romantic night at the Cranberry Inn on Main Street.
By the way, you can launch a skiff, kayak or SUP at the Oyster River Landing off Barn Hill Road and either make your way up the Oyster River or the Mitchell River to the downtown area. A kayak/SUP rental shop is located next to the launch ramp.
No matter how you get there, Chatham is a special place that’s worth the effort.