Breakfast
Eggs and scrapple
A slice of scrapple, a Mid-Atlantic loaf of pork and cornmeal, fried until crisp at the edges and served with eggs and toast.
Local tip Ask for it crisp, and add a little ketchup or syrup if you like.
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 100.4 miles by car in all across 4 days. Distances are straight-line estimates, so allow extra for the streets.
Day 1. The Naval Academy and colonial Annapolis
4 stops · 0.8 mi on footAnnapolis on foot. Start at the Naval Academy on the river, walk into the old town to the State House, visit a Georgian mansion and its garden, and end where the old town meets the water at the city dock.
If you only have half a dayUnited States Naval Academy, then Maryland State House. A naval campus beside the river, then the state capitol with its wooden dome.
- 1Morning
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 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.
Photo: Wikimedia Commons on Wikimedia Commons About 8 min walk0.4 mi - 2MiddayIndoor
Maryland State House
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.
Photo by Terry Granger on Unsplash - Lunch
Cream of crab soup
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 - 3AfternoonIndoor
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 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.
Photo: Pubdog ( talk ) on Wikimedia Commons - Dinner
Maryland crab cakes
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.
About 4 min walk0.2 mi - 4Evening
Colonial Annapolis Historic District
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.
Photo by The New York Public Libra… on Unsplash
If it rains. The Naval Academy grounds are mostly outdoors, so start with the State House and the Paca House under cover and keep the walk down Main Street for a dry hour. The brick sidewalks of the old town can be slick.
Day 2. Fort McHenry, the Inner Harbor and Fells Point
4 stops · 0.9 mi on foot, 22.4 mi by carA day in Baltimore, city and harbor. Start at the five-sided fort that defended the harbor in 1814, move to the Inner Harbor and its aquarium, then end in the old waterfront streets of Fells Point. Take a car or a ride from Annapolis, and check ahead on the road and on parking.
If you only have half a dayFort McHenry, then Inner Harbor. A five-sided fort that defended the harbor in 1814, then the waterfront district around the water basin.
- Drive from Colonial Annapolis Historic DistrictAbout 44 min by car20.3 miWhere Day 1 ended.
- Breakfast
Coffee and a Berger cookie
A Baltimore sweet: a soft shortbread-style cookie topped with a thick layer of dark fudge, with a mug of coffee.
Local tip Buy a box to carry home, since they keep well.
- 1Morning
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 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.
Photo: Benson Lossing on Wikimedia Commons About 11 min by car or transit2.1 mi - 2Midday
Inner Harbor
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.
Photo by Grace Dadson on Unsplash - Lunch
Pit beef
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 - 3AfternoonBook 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 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.
Photo: Matthew Binebrink, CC BY-SA 4.0 on Wikimedia Commons About 15 min walk0.8 mi - 4Evening
Fells Point
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.
Photo by Joey Graziano on Unsplash - Dinner
Steamed blue crabs with Old Bay
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. The aquarium is indoors, so keep it for the wettest hour. Fort McHenry is open to the sky and the wind on the point, so go in a gap in the weather. The old streets of Fells Point are better dry.
Day 3. Over the Bay Bridge to St. Michaels and Oxford
4 stops · 0.3 mi on foot, 47.3 mi by carA car day across the Chesapeake Bay. Drive over the Bay Bridge to the Eastern Shore, spend the middle of the day in St. Michaels and its maritime museum, and end in the small waterfront town of Oxford. Check ahead on bridge traffic and the roads.
If you only have half a daySt. Michaels, then Chesapeake Bay Maritime Museum. A small waterfront town in Talbot County, then a museum of bay boats on Navy Point.
- Drive from Fells PointAbout 47 min by car23.3 miWhere Day 2 ended.
- Breakfast
Ham biscuit and eggs
A warm split biscuit with salty country ham and a soft egg, a plain breakfast before the bridge.
Local tip Eat well, since the shore roads have fewer places to stop.
- 1Morning
Chesapeake Bay Bridge
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.
Photo by Mary Oakey on Unsplash About 39 min by car16.5 mi - 2Midday
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 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.
Photo: Famartin, CC BY-SA 4.0 on Wikimedia Commons - Lunch
Oysters
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 - 3AfternoonIndoor
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 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.
Photo: Wikimedia Commons on Wikimedia Commons About 27 min by car or transit7.4 mi - 4Evening
Oxford
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.
Photo: Wikipedian1234, CC BY-SA 3.0 on Wikimedia Commons - Dinner
Rockfish
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.
_at_Spencer_Drive_in_Saint_Michaels,_Talbot_County,_Maryland.jpg){kind=link}
If it rains. Rain and wind can slow the Bay Bridge crossing, so check ahead before you set off. The maritime museum has indoor rooms and outdoor boats, so go in first and walk the docks in a dry spell. Oxford can be skipped in a storm.
Day 4. Harriet Tubman country and Blackwater
4 stops · 0.5 mi on foot, 30.7 mi by carA second car day, south into Dorchester County. Begin at the visitor center that tells the story of Harriet Tubman, walk the park around it, then drive into the marsh of Blackwater and finish in the river town of Cambridge. The roads are long, so check ahead.
If you only have half a dayHarriet Tubman Underground Railroad Visitor Center, then Blackwater National Wildlife Refuge. A history museum on the life of Harriet Tubman, then a refuge of marsh, fields and forest.
- Drive from OxfordAbout 40 min by car16.8 miWhere Day 3 ended.
- Breakfast
Pancakes and eggs
A big plate of pancakes and eggs with syrup and coffee before a day in the marsh.
Local tip Eat well and carry water, since there is little to buy near the refuge.
- 1MorningIndoor
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 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.
About 9 min walk0.5 mi - 2Midday
Harriet Tubman Underground Railroad National Historical Park
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.
Photo: National Park Service on Wikimedia Commons - Lunch
A packed picnic lunch
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.
About 15 min by car or transit3.3 mi - 3Afternoon
Blackwater National Wildlife Refuge
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.
Photo: Jcantroot on Wikimedia Commons About 32 min by car or transit10.6 mi - 4Evening
Cambridge
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.
Photo: Wikimedia Commons on Wikimedia Commons - Dinner
Smith Island cake
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.
.jpg){kind=link}
If it rains. The visitor center is indoors, so keep it for the wettest hour. The park and the refuge are open to the sky with few shelters, so shorten the day and stay in the car in a storm. Check the road ahead.
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 4 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 100.4 miles by car in all across 4 days. Distances are straight-line estimates, so allow extra for the streets.
Keep exploring
Nearby trips
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 like this
More Culture & Discovery trips ›More trips in United States ›
Make this plan yours
Make it yours in a minute, then move days around and add what you want.
A trip idea · Updated November 2026
Want your own days planned like this? Plan your own trip on the web or get the Archie app.