Photo: Don Ramey Logan, CC BY 4.0 on Wikimedia Commons
The 4-day plan, rearranged for 5 days: every place stays and a few more are added, and each day keeps to one part of town.
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.
How much walking? On foot, about 0.3 to 0.9 miles a day, and 156.2 miles by car in all across 5 days. Distances are straight-line estimates, so allow extra for the streets.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
The parish church of Annapolis, an Episcopal church on Church Circle, founded in 1692 as the first church in the town and still in use.
Go when Morning, outside the hours of services.
Local tip The parish church of Annapolis, founded in 1692, stands on Church Circle. It is a working church, so keep your voice low and check ahead on whether visitors can go in.
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 when Midday, 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.
The state of Maryland's official museum of African American history and culture, in the former Mount Moriah African Methodist Episcopal Church. It is named for Benjamin Banneker, Frederick Douglass and Harriet Tubman.
Go when Midday, as an indoor stop.
Local tip The state museum of African American history and culture, in a former church. Take your time with the displays, and check ahead on the opening.
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 when Late 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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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 when Morning, 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.
One of the chapels on the grounds of the United States Naval Academy, used for Protestant and Catholic services. It is on the academy grounds, so visitor access has security checks.
Go when Morning, as part of the academy visit.
Local tip Part of the grounds of the Naval Academy, so the same security checks apply. It is a chapel, so keep your voice low and check ahead on whether you can go in.
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 when Afternoon, 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.
A historic house museum at 19 Maryland Avenue, built in 1774, one of the colonial houses of Annapolis still standing, with a carved doorway on the front.
Go when Afternoon, as an indoor stop.
Local tip A Georgian house built in 1774, now a museum. Look at the front doorway and the rooms inside, mind the stairs, and check ahead on tours.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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 when Morning, 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 when Midday, 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.
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 when Afternoon, 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 when Late 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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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 when Morning, 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.
A national park of fields and marsh beside the visitor center, set aside to honor Harriet Tubman and the landscape she knew. Walk it slowly and respectfully, take water, and check ahead on what is open.
Go when Midday, with a hat and water.
Local tip A landscape of fields and marsh with little shade. Walk it slowly and respectfully, and check ahead on what is open and on the road.
Sandwiches, fruit and water bought in the morning for the park and the refuge, where there is little to eat nearby.
Local tip Pack out what you pack in, and keep food away from the wildlife.
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 when Afternoon 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.
The county seat of Dorchester County, a river town on the Choptank. End the day on its waterfront with a slow walk before the drive home. Check ahead on the road back.
Go when Early evening (about 7:14 PM), on the waterfront.
Local tip A river town to end the day in. Walk the water edge before the drive back, and check ahead on the road home, which is long and unlit in places.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
The dual-span bridge over the bay, opened in 1952, that joins the Western Shore near Annapolis with the Eastern Shore. It is a long crossing, and traffic can back up on summer weekends, so check ahead before you set off. The driver keeps eyes on the road, and passengers get the view.
Go when Morning, before the day traffic builds.
Local tip A long crossing, so fill the tank and carry water first. Traffic can back up on summer weekends, so check ahead. The driver watches the road, and passengers get the view.
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 when Midday, 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.
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 when Afternoon, 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 small waterfront town and former colonial port in Talbot County. Walk its short streets to the water and slow down at the end of a car day.
Go when Late afternoon into evening (about 7:14 PM), as the water turns gold.
Local tip The town is small and easy on foot. Walk to the water and sit for a while. It is a short drive, so you can skip it if the day has run long.
Rockfish, the local name for striped bass, broiled or pan-seared and served with corn and tomatoes in season.
Local tip Ask whether the fish is local and what is in season.
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.
It covers 5 days in Annapolis, planned for september to October. Each day is built around a small number of stops, with room to rest.
It was planned for most travelers. The pace and the places reflect that, so check it fits how you travel.
No. Places marked "book ahead" need a reservation. Hours, prices and availability change, so confirm before you go.
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.
Yes. It is a starting point you can change to fit your own trip: swap a place, add a day or move the pace.
On foot, about 0.3 to 0.9 miles a day, and 156.2 miles by car in all across 5 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 awayMore Culture & Discovery trips ›More trips in United States ›
Make it yours in a minute, then move days around and add what you want.
A trip idea · Updated November 2026
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