Great town with great atmosphere but only sort of good for provisioning. The grocery store is over a mile walk from the nearest dinghy dock. That's a long hike to me. There is a trolley that will take you to the grocery but I've yet to figure it out, we just use our bikes instead. Need to explore that further. Banks, drugs, hardware, marine supplies are available, tho again not a short walk. Best to figure out the trolley!
Free anchoring space is somewhat limited.
There is a bus that will take you to a mall.
If you are an SSCA member the local cruising stations will provide support.
Anchor in Back Creek and dinghy up to the bulkhead above the power sub-station. Less than 1/2 mile walk to groceries, an excellent Chinese restaurant, Quantum Sails, and Fawcett. West Marine is another quarter mile adjacent to a laundromat. CVS is close.
Anchor in Spa Creek, the South Anchorage, or grab a mooring in the main field and the tourist center at the Harbormaster's office has maps and guidance for buses, the Circulator, and the eCruiser. Laundry in the Harbormaster's office. Good bus transportation to local mall and Sam's Club.
Weem's Creek has easy access to a local grocery.
Herrington harbor North - south of Annapolis has a West Marine on-site, but no groceries.
Edgewater has Fawcetts, West and groceries about a mile away. Chesapeake Harbour in Edgewater may have a courtesy van and has laundry on-site but no fuel.
HHN is in Deale, MD. Great boat services and a West Marine, but no provisioning of significance.
Fawcetts, West Marine, groceries, laundry and Chesapeake Harbour are all in Eastport.
Edgewater does have a West Marine but it's far from the water without ground transportation.