Chincoteague to Philadelphia
Tue Nov 3 – Thu Nov 5, 2026
Two driving days up the Delmarva and across the Delaware Valley. Five states and the District, with real stops in each.
- VA (already counted)
- MD
- DC
- DE
- NJ
- PA
Book tonight
Two rooms — Baltimore for Tuesday, Philadelphia for Wednesday — and the Old Ebbitt reservation for 5:00 p.m. Tuesday.
Everything else on this page works if you improvise. Those three don't.
Tuesday, November 3
Chincoteague → Annapolis → DC → Baltimore 265 mi-
FOOD
6:30 AM: Breakfast — Mr. Baldy's Family Restaurant
Opens at 6 a.m., the only real kitchen running that early on the island. Big portions, island prices.
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1350Drive 2h 45m — US-13 north up the Delmarva, then US-50 west across the Chesapeake Bay Bridge (map). Westbound is free; the toll is eastbound only.
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SIGHT
10:00 AM: Maryland State House, Annapolis
Oldest state capitol still in legislative use, and the room where Washington resigned his commission. Largest wooden dome in the country. Bring ID to get in.
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WALK
10:50 AM: Walk down Main Street to the harbor
Ten minutes downhill from the State House to City Dock. Naval Academy gate is right there if you want to look.
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FOOD
11:30 AM: Lunch — Boatyard Bar & Grill
Jumbo lump crab cakes are the reason to go. Usually a 40-minute wait; midweek in November there won't be one.
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50Drive 45m — US-50 west into DC. Leaving by 1:00 beats the afternoon wall on this road.
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PARK
2:00 PM: Park once, near the Mall
One garage in Penn Quarter or near the Mall. Leave the car there through dinner; everything until 7:00 is on foot.
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MUSEUM
2:15 PM: One Smithsonian — pick a single museum
Air and Space or American History. All free, all close at 5:30. Two in an afternoon means seeing neither.
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RESERVED
5:00 PM, reserved: Dinner — Old Ebbitt Grill
Washington's oldest saloon, open since 1856, directly across from the White House. Dark wood, antique fixtures, raw bar. Reserve this one — it fills every night.
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SIGHT
7:00 PM: The monuments after dark
Lincoln, Vietnam, Korean War, WWII, MLK, Jefferson. All outdoors, all lit, all open around the clock, and nearly empty on a November weeknight. This is the best thing on the whole route.
Lincoln to Jefferson and back is about three miles on foot. If the legs or the weather give out, fetch the car and drive between them instead: there's free street parking along Ohio Drive by the Tidal Basin and near the Lincoln after 6:30 p.m.
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95Drive 1h — I-95 north to Baltimore. Sleep in Fells Point or Inner Harbor. Cheaper than DC, and it takes 45 minutes off tomorrow.
Hotel: not booked yet
Wednesday, November 4
Baltimore → New Castle → Camden → Philadelphia 135 mi-
FOOD
8:00 AM: Breakfast — Blue Moon Cafe, Fells Point
Opens at 7. The Cap'n Crunch French toast is what people drive in for. Small room, so go early rather than at nine.
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95Drive 2h — I-95 north. Northbound out of the DC–Baltimore corridor clears up by 9:30, which is why breakfast is unhurried.
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SIGHT
11:45 AM: Historic New Castle, Delaware
Cobblestone Delaware Street, the Green, and Battery Park along the river. A colonial river town that stayed largely intact. Forty-five minutes on foot covers it, and it beats downtown Wilmington by a mile.
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FOOD
12:30 PM: Lunch — Jessop's Tavern
Colonial tavern on the cobblestones, creaking wood floors, Belgian beer list, and a shepherd's pie that arrives the size of a brick.
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295Drive 50m — east over the Delaware Memorial Bridge (map) ($5), then NJ-295 north. Forty miles through New Jersey on the way, with no detour at all. That puts you in Camden around 2:50; the spare 40 minutes absorbs bridge traffic.
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SIGHT
3:30 PM: Camden waterfront, New Jersey
Battleship New Jersey is docked here, and the view back across the Delaware at the Philadelphia skyline is the actual reason to stop. Late afternoon light does the work.
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BRIDGEDrive 20m — Ben Franklin Bridge (map) ($5) into Old City. Check in, drop the bags.
Hotel: not booked yet -
FOOD
7:00 PM: Dinner — The Plough & the Stars
Old City Irish pub at Chestnut and 2nd, in an old bank building. Open till 2 a.m., so there's no rush getting there.
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SIGHT
9:00 PM: Independence Hall and the Liberty Bell — tonight, not tomorrow
Both lit after dark and both a short walk from dinner. The Liberty Bell Center is glass-walled, so the bell is visible from the sidewalk at any hour, and Independence Hall's exterior is lit too.
Do it now. Thursday morning does not exist, and the timed interior tickets wouldn't fit a forty-minute window anyway.
Thursday, November 5
Philadelphia → PHL 12 mi wheels up at noon-
COFFEE
7:30 AM: Coffee near the hotel
Something quick. Nothing with a wait.
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GAS
8:15 AM: Leave for the airport — fuel up on the way
Twenty minutes clear, forty in traffic. Fill the tank before the return or Budget charges their own rate for it.
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HARD STOP
9:00 AM, hard stop: Return the car, then the shuttle to the terminal
PHL's rental return plus shuttle eats more time than anyone plans for. Nine o'clock is the number, not a suggestion. Follow the Rental Car Return signs; your Budget confirmation has the exact drop-off.
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HARD STOP
12:00 PM, hard stop: Frontier departs
Check the terminal and gate in the Frontier app the night before.
Frontier has no interline agreements. If this flight cancels they cannot put you on another airline — you wait for their next one. Rebook in the app right away, then compare one-way fares on other airlines; a new ticket can beat a day's wait.
What it runs
Two people on top of flights and the rental| Item | Est. |
|---|---|
| Hotel — Baltimore, TueFells Point / Inner Harbor, midweek November | $110–160 |
| Hotel — Philadelphia, WedOld City or Center City | $150–220 |
| Food, three daysSix sit-down meals plus coffee | $400 |
| ParkingAnnapolis $6, DC garage $25–40, Philly overnight $45–60 | $105 |
| GasAbout 410 miles | $55 |
| TollsDelaware Memorial $5, Ben Franklin $5 | $10 |
| Museums and monumentsSmithsonians, State House, all memorials | $0 |
| Total | $830–950 |
Why DC comes first
Washington sits west of the Chesapeake; Delaware, New Jersey and Philadelphia all sit on one line northeast of it. Hitting Delaware before DC would cost four hours of backtracking, and running DC as a day trip from Philly would cost five. The order is set by the map, not by preference.
Map links open Google Maps. Times are Eastern.