HappeningStill warm, with the heat easing. Defenders Day events at Fort McHenry mark the defense of 1814 (dates vary). Fall bird migration begins at Blackwater.
From average weather, 2021 to 2025: days that are warm but not hot, with few rainy days, score highest. Crowds and prices change through the year, so check them before you book.
Arrival day
Before Day 1. Annapolis is a small old town of brick sidewalks, so a room within a short walk of the harbor saves the car for later.Details
Flying in
The nearest large airport to Annapolis is Baltimore/Washington International. A rental car is the easiest way to do this guide, since Days 3 and 4 are car days, and a rideshare or a booked ride also works for the first leg.
By train or bus
Annapolis has no train station. Come by train to Baltimore, or to the Washington area, and carry on by rental car, bus or rideshare. Check ahead on the connection, and book the car for Days 3 and 4.
What to pack
Comfortable shoes for brick sidewalks that are uneven in places, a light rain jacket, and a hat and water for the marsh and the docks. Summers are hot and humid, and the bay wind is cool in spring and fall.
Day 1 starts nearby
Day 1 begins at the Naval Academy and ends at the city dock, so settle in, then walk down Main Street to the harbor basin for a first look at the water.
How much walking? On foot, about 0.3 to 0.9 miles a day, and 135.7 miles by car in all across 3 days. Distances are straight-line estimates, so allow extra for the streets.
Day 1. Annapolis and the Naval Academy
4 stops · 0.8 mi on foot
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
1
Morning
United States Naval Academy
The service academy for future naval officers, founded in 1845 and set on a waterside campus at the edge of the old town. Walk the grounds, look in at the chapel and the museum, and take your time. Visitor access has security checks, so check ahead on how to enter and what you need to bring.
Go whenMorning, before the grounds fill up.
Local tip It is a working military school, so expect security checks at the gate. Check ahead on how visitors get in and what you need to bring, and wear shoes for a long walk on the grounds.
The state capitol, begun in 1772 and still used by the Maryland General Assembly. It is said to be the oldest state capitol in continuous legislative use, and in 1783 and 1784 the national Congress met here. Look up at the wooden dome. It is a working government building, so check ahead on visits and screening.
Go whenMidday, as an indoor stop.
Local tip Walk around the outside first and look up at the dome. It is a working government building, so check ahead on visits and screening, and be polite to the staff.
A rich, creamy soup of lump crab, a bowl for a cool day in the old town.
Local tip Ask for a small cup first, since it is filling.
About 4 min walk0.2 mi
3
AfternoonIndoor
William Paca House and Garden
A Georgian mansion built between 1763 and 1765 for William Paca, who signed the Declaration of Independence and became governor of Maryland. The walled garden behind it has been restored. Check ahead on tours, and mind the steps.
Go whenAfternoon, as an indoor stop with a garden.
Local tip See the rooms, then take the garden at the back slowly. There are stairs inside, so check ahead on tours and on step-free access.
The old town, a National Historic Landmark district of narrow streets and colonial houses. Walk Main Street downhill to the city dock, the small harbor basin at its foot, and watch the boats come and go as the light drops.
Go whenLate afternoon into evening (about 7:14 PM), when the light softens on the water.
Local tip Walk Main Street downhill to the city dock and sit by the basin to watch the boats. The brick sidewalks are uneven, so watch your step.
Lump crab bound with very little filling, broiled or fried, a dish of the bay and of Annapolis.
Local tip Look for a cake that is mostly crab, with little filler, and eat it hot.
If it rains. Maryland State House and William Paca House and Garden are covered, so keep them. Move United States Naval Academy and Colonial Annapolis Historic District to a dry day if you can.
Day 2. The Baltimore harbor
4 stops · 0.9 mi on foot, 22.4 mi by car
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
Drive from Colonial Annapolis Historic DistrictAbout 44 min by car20.3 mi
Where Day 1 ended.
1
Morning
Fort McHenry
A pentagonal fort on Locust Point, built in 1798 and known for the defense of Baltimore harbor against the British navy in September 1814. It is a national park site, so go in a respectful mood and read the displays. There is little shade on the grounds, so take water and check ahead on the opening.
Go whenMorning, before the sun is high.
Local tip Read the story of September 1814 before you walk the walls. There is little shade and the wind off the water can be strong, so take a layer and water, and check ahead on the opening.
The old seaport at the heart of Baltimore, now a waterfront of promenades, ships and museums at the mouth of the Jones Falls. Walk the water edge, look at the boats and let the middle of the day pass slowly.
Go whenMidday, with a walk along the water.
Local tip Walk the promenade and look at the ships. It is busy on a fair weekend, so keep your valuables close and plan a rest on a bench.
A Baltimore roadside sandwich of beef grilled over charcoal, sliced thin and piled on a roll with raw onion and a sharp horseradish sauce.
Local tip Go easy on the horseradish the first time, since it is strong.
About 4 min walk0.2 mi
3
AfternoonBook aheadIndoor
National Aquarium
A public aquarium on Pier 3 of the Inner Harbor, open since 1981. Fish, sharks and reef animals fill the tanks across several levels. Entry is by ticket, so check ahead, and it is an indoor stop for a wet or hot hour.
Go whenAfternoon, as an indoor stop for a wet or hot hour.
Local tip Entry is by ticket, so check ahead on timed entry. Choose the levels that catch your eye rather than trying to see them all.
A historic waterfront neighborhood east of downtown, established around 1763 and known for its maritime past. Old brick and stone streets, uneven in places, run down to the harbor. Walk to the water and look at the old buildings.
Go whenLate afternoon into evening (about 7:14 PM), when the waterfront lights up.
Local tip Walk down to the water along the old streets, which are uneven in places. Look at the brick houses and the old buildings, and leave time to simply sit.
Whole blue crabs steamed and heaped with Old Bay seasoning, eaten by hand with a mallet at a paper-covered table, a Chesapeake ritual.
Local tip Wear something you can spill on, expect a slow and messy meal, and ask how it is done.
If it rains. National Aquarium is covered, so keep it. Move Fort McHenry, Inner Harbor and Fells Point to a dry day if you can.
Day 3. Dorchester County, Tubman country and Blackwater and St. Michaels, Oxford and the Bay Bridge
4 stops · 0.3 mi on foot, 113.3 mi by carAbout 3 h 14 min driving
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
Drive from Fells PointAbout 1 h 35 min by car62.8 mi
Where Day 2 ended.
1
MorningIndoor
Harriet Tubman Underground Railroad Visitor Center
A visitor center and history museum in Church Creek that tells the story of Harriet Tubman, who was born enslaved in this county and became a leader of the Underground Railroad. Come with time to read and to reflect, and check ahead on the opening.
Go whenMorning, when you have time to read.
Local tip Allow a slow visit and read the displays. The story is of slavery, flight and courage, so go in a respectful mood. Check ahead on the opening.
About 48 min by car23.9 mi
2
Midday
St. Michaels
A small town in Talbot County, named for the church founded there in 1677, with a long history of shipbuilding on the water. Walk its streets down to the harbor and browse at an easy pace.
Go whenMidday, with a walk to the harbor.
Local tip Park once and walk. The streets run down to the water, so look at the old houses and the boats at the dock, and check ahead on the road if rain is forecast.
Oysters of the bay, served raw on the half shell, fried or baked, a long tradition of the Eastern Shore towns.
Local tip Oysters are traditionally eaten in the cooler months, so ask what is in season. Skip raw ones if you are unsure.
About 6 min walk0.3 mi
3
AfternoonIndoor
Chesapeake Bay Maritime Museum
A museum on Navy Point, founded in 1965, with a large collection of Chesapeake Bay boats in and around many buildings. Hooper Strait Light, a screw-pile lighthouse that once stood in the bay, is an exhibit on the grounds. Check ahead on the opening.
Go whenAfternoon, with both indoor and outdoor parts.
Local tip Look at the boats and the lighthouse on the grounds, then walk the docks. Wear a hat for the outdoor parts, and check ahead on the opening.
A refuge of freshwater pools, tidal marsh, open fields and forest, set up in 1933 as a sanctuary for birds on the Atlantic Flyway. Drive its loop slowly, stop to look for waterbirds, and take a hat, water and insect repellent. Check ahead on access and the roads.
Go whenAfternoon into evening (about 7:14 PM), as the birds move.
Local tip Drive slowly with the windows down and stop at the pull-offs. Take a hat, water, binoculars if you have them, and insect repellent in warm months. Check ahead on access.
A tall cake of many thin layers of yellow cake with fudge icing, from Smith Island in the bay, a Maryland dessert to end the trip.
Local tip Buy a slice to share, since it is large.
If it rains. Harriet Tubman Underground Railroad Visitor Center and Chesapeake Bay Maritime Museum are covered, so keep them. Move St. Michaels and Blackwater National Wildlife Refuge to a dry day if you can.
Departure day
After the last day. Day 4 ends in Cambridge, on the Eastern Shore, so leave time for the road back across the Bay Bridge.Details
Heading to the airport
Plan the drive back around the Bay Bridge and the roads to the airport with time to spare. Bridge traffic can back up, so check ahead on the day, and fill the tank and return the car before your flight.
Something to pack
A tin of Old Bay seasoning, a Berger cookie box and a print of a bay lighthouse are all easy to carry. Wrap anything fragile well.
If you have a few hours
Take one more slow walk down Main Street to the city dock in Annapolis, or the waterfront of Fells Point in Baltimore, and watch the boats before you go.
Questions people ask
When is the best time to visit Annapolis?
By average weather from 2021 to 2025, April to May and September to October are the most comfortable months for walking around Annapolis. This plan is built for september to October, which is one of the best months. Crowds and prices change through the year, so check them before you book.
How many days does this plan cover?
It covers 3 days in Annapolis, planned for september to October. Each day is built around a small number of stops, with room to rest.
Who is this plan for?
It was planned for most travelers. The pace and the places reflect that, so check it fits how you travel.
Is anything on this plan booked?
No. Places marked "book ahead" need a reservation. Hours, prices and availability change, so confirm before you go.
Can I plan my own days like this?
Yes. Archie drafts a day by day plan for your dates and takes your pace, the weather and who is travelling into account. You can start one from the Archie app.
Can I change this plan?
Yes. It is a starting point you can change to fit your own trip: swap a place, add a day or move the pace.
How much walking is there?
On foot, about 0.3 to 0.9 miles a day, and 135.7 miles by car in all across 3 days. Distances are straight-line estimates, so allow extra for the streets.
3 days of monuments and picnics in Washington, DCAbout 40 miles awayAn easy add-on
3 days of slow beach time on the Delaware shoreAbout 70 miles away
3 days of Victorian streets, lighthouses and beach timeAbout 80 miles away
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