Boston by Orange Line - Food, History, and Stops Worth Getting Off At

You can drive from Washington to Boston in about seven hours if the traffic gods are feeling generous, which they almost never are on I-95 through Connecticut. The train takes roughly six and a half on the Acela, and the flight is barely an hour in the air, though you'll spend almost as long again just getting through security at Reagan. For a retired teacher like me, the calculation comes down to something simpler than time: what do I want to do at the other end, and how much patience do I have left when I get there?

The common advice says fly, and for most people that's probably right, especially if you're only going for a weekend. Cheap flights Washington, D.C. — Boston make that option tempting, but here's the thing nobody tells you about the short hop from D.C. to Boston: the flight is a bit under two hours door to door when you count everything, and the Orange Line from Back Bay to the airport adds another forty minutes on the way in. I've done the trip both ways more times than I can count, and I keep coming back to the same conclusion — the best approach depends entirely on whether you're chasing food or chasing history.

If you want the food, fly into Logan and take the Silver Line into the city, because the Orange Line drops you right in the middle of some of the best eating in Boston. Get off at Chinatown station and you're steps from the dumpling houses on Beach Street, or ride two more stops to Tufts Medical Center and walk over to the South End's tapas places on Tremont. A friend of mine swears by the roast duck at a place on Tyler Street that's been there since the 1980s, and you can't get within a mile of that experience if you've driven, because you'd be circling for parking the whole time anyway.

For the history, though, the Orange Line is oddly better than you'd expect, even if the Freedom Trail itself is a Red Line thing. Get off at State Street and walk ten minutes to Faneuil Hall, or ride to Haymarket and wander the weekend stalls that have been there since the 1700s; the station itself sits on ground that was literally filled in from the hills that used to be Boston. The line runs through the old heart of the city, and you'll see more of the brick and cobblestone character in one stop than you would in a week of driving around the suburbs.

• Check the fare search before you commit to anything, because prices swing wildly between Tuesday morning and Friday afternoon
• Consider whether you're willing to pay $40 a day for downtown parking, because that will eat any savings from driving
• Pack light if you're flying, since the Orange Line and the Silver Line both have limited luggage space
• Decide what matters more: the food walk or the history walk, because they pull you in different directions
• Look at the weather, because a rainy day in Boston means you'll want the underground access

The honest truth is that driving wins if you're bringing the family or if you're planning to visit the suburbs outside the city itself. The parking situation at the airport is miserable, but the garages at the Orange Line stations are cheap and safe, and you can leave the car there for the weekend without worrying about it. I've done the drive myself plenty of times, and there's something to be said for having your own car when you want to get out to Cambridge or Somerville for dinner.

But for a solo traveler or a couple who wants to eat well and walk the Freedom Trail, the flying-plus-transit approach is hard to beat, especially if you're flexible on dates like I am now that I'm retired. Midweek flights on this route regularly drop below $80 each way if you book a few weeks out, and I've seen them as low as $59 in September when the summer crowds have gone. You can book Washington to Boston for less than the cost of the gas and parking, and that's before you factor in the tolls on the Jersey Turnpike.

The real question isn't which method is cheaper or faster, because that depends on the week and the season and whether you can move your dates around. It's whether you want to arrive in Boston ready to walk, or whether you'd rather have the car waiting in the garage when you're done.