You think you know Annapolis, but have you experienced the Countryside? From bayside harbours to historic artifacts and landmarks, the Annapolis Countryside has many hidden gems for friends and families alike to enjoy.

Cross over the South River Bridge from downtown Annapolis and, almost immediately, things start to feel different. The traffic dwindles, the pace slows, and you soon find yourself in the beautiful, pristine Annapolis Countryside, where much of what you'll witness appears as if time has stood still for hundreds of years. But even as you glimpse horses grazing on farmland and quaint 19th century bungalows with hammocks hanging from porches, within minutes you can arrive at a luxurious, modern, eco-friendly waterfront resort. Whether with the whole family, or taking some time alone with a significant other, a night or two in the countryside supplies the relaxation you're looking for. 

Enjoy the Annapolis Countryside with the aid of this two-day itinerary:

Day One

Waterfront dining

Check in at the quaint, Bayside Herrington Harbor Inn. Eco-friendly with access to the beach and Chesapeake Bay, it's the ideal location to stay while touring the Countryside. Stop by Historic London Town and Gardens to get a taste of what life was like for the Bay's first settlers. A small, fully functional village is open for visitors, accompanied by an impressive, 18th-century waterfront home. The site also encompasses an interactive archaeological center, where visitors can view all the artifacts dug up from London Town. Get back to the hotel for lunch before renting a kayak or paddleboard and hitting the water. Or, just relax on the beach taking in the Maryland sunshine before dinner at the hotel or a restaurant.

Day Two

Fishing on the Bay

Enjoy breakfast before heading out to explore the countryside. Depending on what you're looking for, there's a ton of things to do. Visit a maritime village to learn a little about the fishing, oystering, and crabbing heritage of the Chesapeake Bay region. Grab lunch before climbing aboard one of the many charter boats docked in the countryside and spend the day reeling in Maryland's famous striped bass. Some local restaurants will even cook your freshly caught fish right after the trip. Or, head to Chesapeake Beach to shop or let the kids loose at the water park before a Bayside dinner. Visit a maritime village to learn a little about the fishing, oystering, and crabbing heritage of the Chesapeake Bay region.

As you are heading home, stop by Greenstreet Gardens on the way. This full service Garden Center featues a gift shop and seasonal events for the whole family to enjoy. If you're here during the fall make sure to check out their fall festival.