Is there a train to Annapolis?

No, there is no direct train service to Annapolis.

How long is the drive?

The drive takes about 1.5 hours.

What is the best way to get around?

A car is not necessary for the historic district; walk or use the free shuttle.

Annapolis is generally safe, but like any city, use common sense.

Middletown

Annapolis

Driving

Middletown to Annapolis

Updated: 28 May 2026

The drive from Middletown to Annapolis is a short 100-kilometer journey. The most direct route involves taking US-301 South through Maryland. Annapolis, the capital of Maryland, is known for its historic district, the U.S. Naval Academy, and its beautiful waterfront. This route is a popular day trip for those in the Mid-Atlantic region.

Total Distance: 100 km driving distance; 80 km straight-line air distance.

Fastest Way

Driving via US-301 is the fastest route, taking about 1.5 hours.

Cheapest Way

Driving is the only practical way to reach Annapolis from Middletown.

Compare Middletown to Annapolis Routes

Driving

Direct

Duration

1 hour 30 mins

Avg Price

$15 - $30 (fuel)

Operator

Personal Vehicle

Route

US-301 S.

Prepare for potential traffic on US-301.

Travel Tips

Parking
Parking in the historic district can be difficult; use public parking garages.
Weather
Annapolis has a mild climate; it is always a good time to visit.
Transportation
A car is not necessary for the historic district; walk or use the free shuttle.
Dining
Try the local seafood; Annapolis is famous for its crab cakes.
Events
Check the city calendar for festivals and events in the historic district.

Safety Tips

Driving Safety
Stay alert on US-301; take regular breaks.
City Safety
Stay aware of your surroundings in busy tourist areas.
Emergency Prep
Keep a roadside assistance plan for the drive.