A two-week one-way trip from New York to Boston: three days on foot in Manhattan, then the car for Philadelphia, Washington, Shenandoah's Skyline Drive, Annapolis, the Hudson Valley, Newport and Cape Cod. From the cities of Independence to the Blue Ridge crests and the Atlantic lighthouses, on toll roads that are paid almost everywhere without booths, by E-ZPass electronic toll.
| Days | Stop | Drive |
|---|---|---|
| Days 1 to 3 | New York | Start |
| Day 4 | Philadelphia | 152 km · 2h05 |
| Days 5 to 6 | Washington | 217 km · 3h |
| Days 7 to 8 | Luray (Shenandoah) | 183 km · 3h |
| Day 9 | Annapolis | 253 km · 3h35 |
| Day 10 | Tarrytown | 386 km · 5h |
| Day 11 | Newport | 262 km · 3h35 |
| Days 12 to 13 | Chatham (Cape Cod) | 147 km · 2h15 |
| Day 14 | Boston | 142 km · 2h |
Road route calculated from the stops (OpenStreetMap). Driving times assume no stops and no traffic: add time for photo breaks.
Mid-May to June and September to mid-October: the autumn colour season in Shenandoah runs from late September to November, and services on Cape Cod are still open. July is the most expensive month to hire a car ($104 a day in New York); in winter, the Skyline Drive closes in sections with every spell of snow or ice, and park services close in November.
🚗 152 km · 2h05 of driving from New York
Car picked up at Newark airport, then the New Jersey Turnpike (I-95) south: tolls by transponder or by plate.
🚗 217 km · 3h of driving from Philadelphia
I-95 through Delaware ($5) and the Baltimore tunnels, then the Baltimore-Washington Parkway. In the city, leave the car parked.
🚗 183 km · 3h of driving from Washington
I-66 to Front Royal, then the Skyline Drive along the ridges to Thornton Gap (35 mph), and US 211.
🚗 253 km · 3h35 of driving from Luray
US 340 through the Shenandoah Valley and Harpers Ferry, then the I-70, the Baltimore Beltway and the I-97.
🚗 386 km · 5h of driving from Annapolis
I-95 via Baltimore and Delaware, the New Jersey Turnpike, then the George Washington Bridge and the Thruway: the most expensive day for tolls.
🚗 262 km · 3h35 of driving from Tarrytown
I-287 then the I-95 along Connecticut; in Rhode Island, Route 138 and its two bridges to Jamestown and Newport, the second one tolled.
🚗 147 km · 2h15 of driving from Newport
Route 24 and I-195, the Bourne Bridge over the Cape Cod Canal, then US 6: traffic jams in summer, especially at weekends.
🚗 142 km · 2h of driving from Chatham
US 6, the Sagamore Bridge and Route 3 north. Return the car on arrival: Boston is best seen on foot and by subway.
Keep New York (3 nights), then pick up the car at Newark for Newport, Cape Cod and Boston (7 nights in all). Or do the southern half, from New York to Washington and Shenandoah, returning the car in Washington.
| Car, New York, January | ≈ $51 a day (€45) |
|---|---|
| Car, New York, July | ≈ $104 a day (€91) |
| Small car, New York | ≈ $64 a day (€56) |
| SUV, New York | ≈ $92 a day (€81) |
| Annual average, New York | ≈ $84 a day (€74) |
| Vehicle | Small car or saloon: everything is paved, and a small car is easier to park in town. |
|---|---|
| Where to pick it up | At Newark airport (EWR) on the day you leave New York, returned in Boston (Logan): one way. |
| One-way fee | Hertz charges a fee for returning in another city: the amount varies by rental company, so compare the total price. |
| Electronic tolls | Accept the rental company's programme: Hertz recharges tolls at the full, undiscounted rate, plus service fees. |
| Insurance | Take the LDW or CDW (damage to the vehicle) and extended liability cover (LIS or SLI). |
| Age | 20 at Hertz, 21 at Enterprise; a surcharge of about $25 a day under 25. |
| Licence and card | Hertz requires a passport in the same name as the licence; an International Driving Permit alone is not enough. |
| Prices quoted | Kayak averages in New York, September 2026, excluding one-way fees, tolls and insurance. |
⚠️ The New York to Boston one-way trip adds a one-way fee, and tolls are recharged with fees: compare the total price, not the daily rate.
For a tourist stay on an ESTA. An International Driving Permit is strongly recommended.
As in mainland Europe. Almost all hire cars are automatic.
65 mph in New York, New Jersey and New England, 70 in Pennsylvania, Maryland and Virginia; 35 on the Skyline Drive.
0.08% in every state on the route, zero tolerance under 21.
Bridges, tunnels and motorways in the North-East, often without booths: without a transponder, the bill follows the plate.
South of 60th Street, 05:00 to 21:00 on weekdays; $2.25 at night. Set off from Newark.
In New York unless signed otherwise, in Washington since 2025. Elsewhere, allowed after stopping, unless there is a NO TURN ON RED sign.
When every approach has a stop sign; if you arrive at the same time, the vehicle on the right goes first.
As long as its red lights are flashing, except on a dual carriageway.
Handheld phones banned in every state on the route, in Pennsylvania since June 2025.
≈ €0.98 to €1.05 per litre depending on the state ($4.24 to $4.55 a gallon, AAA, 24 September 2026)
Price recorded in September 2026: it changes every week, sometimes by 10 to 20 cents in a month. Today's price: AAA Gas Prices →
⛽ 1,742 km at 7 l per 100 km: about €130 at September 2026 prices, to share between passengers.
Virginia is the cheapest, Pennsylvania the most expensive. Few filling stations on the Skyline Drive: fill up before going up. Foreign card: pay at the counter.
| New Jersey Turnpike | Up to $21.88 by transponder, $22 in cash (2026 rate) |
|---|---|
| I-95 in Delaware (Newark) | $5 each way |
| Baltimore tunnels (I-95, I-895) | $4 by non-Maryland transponder, $6 by plate, no booths |
| I-95 north of Baltimore (Perryville) | Northbound only, no booths |
| Delaware Memorial Bridge | Toll towards Delaware only: free in the direction of the route |
| George Washington Bridge | $14.79 to $16.79 with an NY/NJ transponder, $23.30 by mail, towards New York only |
| Manhattan congestion zone | $9 a day by transponder, from 05:00 to 21:00 on weekdays |
| Pell Bridge (Newport) | $4 with a non-Rhode Island transponder, $6 without |
| Cape Cod bridges (Bourne, Sagamore) | Free |
| Skyline Drive (Shenandoah) | $30 per vehicle for 7 days, card only |
| Harpers Ferry | $20 per vehicle for 3 days |
| Fort McHenry | $15 per adult, free under 16 |
| Cape Cod National Seashore beaches | $25 per vehicle per day, from late May to mid-September, card only |
| Independence Hall | Free, $1 booking fee |
| America the Beautiful pass for non-residents | $250: pointless here, no park on the route applies the $100 surcharge |
| Skyline Drive (Shenandoah) | Closed in sections at any time in case of snow or ice |
|---|---|
| Skyland services (Skyline Drive) | Open from 30 March to 8 November 2026 |
| Big Meadows services (Skyline Drive) | Open until 29 November 2026, including the Byrd Visitor Center |
| Province Lands Visitor Center (Provincetown) | Open from May to October only |
| Annapolis Naval Academy | Closed to foreign visitors without a military escort |
| Sagamore Bridge (Cape Cod) | Rebuilding planned from 2027, current bridge open during the works |
Two weeks to link New York to Boston via Washington and Shenandoah: 14 nights, nine stages, including three nights in New York without a car. Drives rarely take more than three to four hours, except Annapolis to Tarrytown, the longest. In eight days, keep New York, then Newport, Cape Cod and Boston.
Excluding flights and accommodation: $560 to $1,150 for eleven days of car hire (Kayak, New York, September 2026), plus one-way fees; about €130 of petrol at September 2026 prices for about 1,750 km; tolls at every major crossing (George Washington Bridge $16.79 to $23.30, New Jersey Turnpike up to $22); $30 for the Skyline Drive.
No. Subway, buses and walking are enough, and parking is expensive. Driving into Manhattan south of 60th Street also costs $9 a day by transponder. See New York first, then pick up the car at Newark airport, linked to Manhattan by train, on the day you leave for Philadelphia.
Many bridges and tunnels in the North-East no longer have booths: E-ZPass or a bill by plate. With a hire car, the simplest is the rental company's programme; at Hertz, tolls are recharged at the highest rate, plus service fees. E-ZPass discounts on the George Washington Bridge are reserved for New York and New Jersey accounts.
Mid-May to June and September to mid-October. Autumn colours reach Shenandoah from late September to November, with no predictable peak date. In July, car hire reaches $104 a day in New York and the Cape Cod bridges are jammed at weekends. In winter, the Skyline Drive closes in sections with every snowfall.
Yes, that is the idea of this itinerary: it saves driving more than 300 km back. The rental company charges a one-way fee, which varies from one company to another and is sometimes high: compare the total price of the hire, not the daily rate, and check that mileage is unlimited.
Driving rules, prices and closures checked in September 2026; hotels checked on OpenStreetMap and then on Booking. Rules change: read the official source before you leave, and check your own government's travel advice for the country. Stop photos: Wikimedia Commons, authors and licences under each image.
Off We Gooo road trip guide · offwegooo.com/en/road-trips/us-east-coast · by Tom, updated 1 October 2026
