Annapolis
(Sample Route from the Field Guide)
Maryland’s Historic Maritime Capital
Annapolis blends colonial history, waterfront culture, and access to Central Maryland’s emerging wine landscape. As the state capital and a Chesapeake Bay port city, it offers a refined and walkable starting point before venturing into nearby vineyards shaped by water, humidity, and agricultural tradition.
Historic Background
Founded in the 17th century and serving as Maryland’s capital since the colonial era, Annapolis is one of the most historically significant small cities in the United States. Its preserved streets, waterfront harbor, and enduring maritime culture reflect centuries of political, naval, and agricultural influence. The surrounding countryside, shaped by Chesapeake waterways and farming tradition, now supports a growing wine presence within easy reach of the city.
Route Overview
This route explores wineries located within driving distance of Annapolis, where vineyards benefit from the moderating influence of nearby waterways and Chesapeake Bay breezes.
The route combines three wineries offering different tasting environments, from relaxed farm vineyards to more structured educational tasting experiences.
Estimated Total Experience Time
Approximately 4-5 hours, allowing time for lunch, relaxed tastings, and scenic drives through the surrounding countryside.
Optional Morning Exploration
Visitors arriving earlier in the morning may wish to explore historic downtown Annapolis before beginning the wine route.
The city’s compact historic district includes cobblestone streets, colonial buildings, waterfront views, and numerous shops and cafes.
Recommended arrival time: 9:30–11:00 AM
What to See
Maryland State House (the oldest state capitol still in continuous legislative use)
Historic Annapolis District
City Dock and Annapolis Harbor
United States Naval Academy grounds and visitor center
Where to Eat
Recommended lunch options before beginning the wine route:
The Federal House: Located in a historic colonial building overlooking City Dock, The Federal House offers classic American tavern fare and a lively harbor atmosphere in the heart of downtown Annapolis.
Harry Browne’s: A longtime Annapolis institution located across from the Maryland State House, Harry Browne’s is known for refined American cuisine and an elegant dining setting.
The Choptank: A large waterfront seafood restaurant and oyster bar located along the Annapolis harbor, offering expansive views of the Chesapeake Bay and a lively coastal dining atmosphere.
Suggested Route Sequence
11:00 AM — Lunch in Annapolis
Beginning the day with lunch allows travelers to enjoy the historic waterfront district before heading into the surrounding countryside.
12:30 PM — Great Frogs Winery
Drive time from Annapolis: 10 minutes
Address
3218 Harness Creek Rd
Annapolis, MD
Phone
(410) 626-8271
Website
Known for
Estate-grown wines produced on a historic farm property just outside Annapolis.
Tasting Style
Relaxed tastings offered in a rustic tasting room surrounded by vineyards and farmland.
Food
Light snacks available. Outside food permitted in designated areas.
Family Policy
Children are permitted but must be supervised at all times, as the primary focus of the winery is wine production and tasting.
Pets
Dogs allowed on leash in outdoor areas.
2:00 PM — The Vineyards at Dodon
Drive time from Great Frogs: 20 minutes.
Address
391 Dodon Rd
Davidsonville, MD
Phone
(410) 798-1126
Website
Known for
Small-lot wines crafted with a strong focus on terroir and sustainable vineyard practices.
Tasting Style
Educational tastings often paired with vineyard tours and guided experiences.
Food
No regular food service. Picnic-style outdoor gatherings are sometimes offered during warmer months.
Family Policy
Most tastings and events are designed for 21+ visitors, although families may attend certain outdoor gatherings.
Pets
Well-behaved dogs allowed on leash in designated outdoor hillside areas.
Additional Wineries in the Area
Visitors with additional time may also wish to explore several other wineries located within driving distance of Annapolis.
Love Point Vineyards
Chesapeake Manor Vineyard & Winery
These wineries can easily be incorporated into extended visits to the region.
Winery hours and reservation policies may vary.
This route is just one part of the full system.
Inside the Field Guide, you’ll find many more towns, regions, and carefully designed winery routes across Virginia and Maryland—each built for flow, timing, and experience.
A Structured Approach to Wine Travel
Access curated cluster routes, drive-time sequencing, seasonal strategy, and regional context designed for travelers who want to explore Maryland’s wine landscape with clarity and intention.