Last minute short road trip from Philadelphia to Boston
March 12, 2014 11:25 AM   Subscribe

So I think we're going to do a last minute road trip from Philadelphia to Boston and back. Please help us plan.

I saw this but want less focus on Boston, DC, and NYC, and more focus on other places between Philly & Boston.
We specifically DO NOT plan to stop in New York City because we've seen it plenty of times and also I don't plan to drive through.

We'll start early tomorrow morning from Philadelphia, stop somewhere during the day, and end up in Boston around dinner time. Where should we stop?

On the way back, we will leave Boston on Saturday afternoon, spend the night somewhere along the way, and then by Sunday night drive home to Philadelphia, giving us another 24-hours or so to hang out somewhere. Where?

Just looking at the map, Providence or Hartford are places that we might want to check out although I know nothing about either. I don't know what towns to stop in or what to do while there in such limited time and would greatly appreciate the input. Hotel suggestions for our two nights in Boston as well as for the one night we can stop somewhere else are also appreciated.

We like: food, culture, outdoor markets, the outdoors in general, walking around a lot, relaxing. We're not big fans of museums but would do something particularly unique. Thank you for any and all suggestions!
posted by cacao to Travel & Transportation (7 answers total)
New Bedford is cute, if maybe a bit too close (about an hour south) to Boston. Cutesy downtown area, tons of whaling stuff- the whaling museum there qualifies as "unique", I think.

Another possibly is the Pioneer Valley/Five Colleges area. Again, cutesy little downtown areas with various shops and restaurants; there's also hiking in the area.

There's surprisingly good hiking in NJ/NY: if you're looking for a day hike, there's Bear Mountain in NY, the Delaware Water Gap (either NJ or PA side), and South Mountain Reservation in NJ (particularly Hemlock falls), which is close to Montclair (again, nice little downtown; locally known as the place where people from Park Slope go when they have their second child) and West Orange which has the Thomas Edison Memorial Park (you can wander around the old labs, as well as his house).
posted by damayanti at 11:51 AM on March 12, 2014

Hudson, New York or Northampton/Hadley/Amherst Massachusetts might be a good choice in either direction (this is the same as the Five Colleges area mentioned above). They're not right on the way but they take you out of the whole I-95 megalopolis thing that you can get stuck in driving up the east coast. If you go for Western Massachusetts you could get pancakes and see them make maple syrup at the North Hadley Sugar Shack.

Alternately (or when you're going the opposite direction) you might want to stop in one or more of the small cities along I-95 in Connecticut - Mystic, New London, someplace like that. Hartford I'm not a big fan of - I'm sure it has its charms if you know where to look but it feels like all insurance companies and banks to me.

Providence is a nice little city but it's only about 20 minutes closer to Philadelphia than Boston is, so not great from a breaking-up-the-journey perspective (not sure how important that is for you). You could also do Newport, RI.
posted by mskyle at 11:59 AM on March 12, 2014

If I were you, I'd go out of your way to drive through Dutchess County, New York. Lovely hills and farmland and stuff.

I'd echo stopping in the Pioneer Valley. Northampton is lovely.

Bridgeport, CT is kind of an interesting place to stop. Shabby city, but some lovely Frederick Law Olmstead parks, seaside views, and some secret great places to eat.
posted by entropone at 12:50 PM on March 12, 2014

You're doing this tomorrow, March 13th? Keep an eye on the weather. Boston may get a bit of snow. Expect an extra-long drive, at least, and don't plan on feeding the ducks Thursday night.
posted by catalytics at 12:59 PM on March 12, 2014

Don't go through Ft Lee. The traffic is terrible. 😉

Hartford is the best bet, time and route-wise. Not a tourist Mecca, though. There's the Mark Twain house, and a few museums. If you want quaint, it's not a huge detour to Essex.

If you are into very old footprints, look up Dinosaur State Park.
posted by SemiSalt at 2:22 PM on March 12, 2014

Background: I live in MD, family in the NYC area, in-laws in the Hartford area, and lots of friends in the Boston area because I lived there for several years.

Avoid NYC entirely and drive around it. A personal favorite route of mine is to drive up to I-78, pick up 287 into NY, Tappan Zee Bridge and 287 to either 684 or the Saw Mill depending on what mood I'm in, then up to 84 and off into Connecticut.

If you've got time, though, I'll nth a stop in Northampton and/or Amherst.

If you like scenic routes, take the Taconic State Parkway allllll the way up to I-90. If you've got more time, back up to Albany and take I-787 to NYS Route 7 to NYS Route 278 to NYS Route 2 which then becomes Massachusetts Route 2. (You'll have to take I-91 back down to the Amherst/Northampton area.) Mass 2 has some fantastic scenery (particularly in the fall, but that's irrelevant to your trip).

Providence is a nice city and I enjoy it a lot, but it seems a bit too close to Boston to fit in with what time you'd like to stop.

Honestly, despite having family in the area, I haven't spent much time in Hartford itself (the family is in the suburbs). All I've seen of Hartford is the area around the Greyhound station where we dropped my sister-in-law off after Christmas for her to catch a bus home.
posted by tckma at 3:45 PM on March 12, 2014

As a Hartford-area native, let me tell you empatically that it isn't a tourist destination. It's a downtown and quite a bit of poverty and little else. I'd suggest Providence, which has an arty scene, or perhaps something charming along the Connecticut coast. If you're willing to take the long route, Boston Post Road along the coast will take you through a lot of cute towns and offers some nice natural scenery.
posted by charlemangy at 4:56 PM on March 12, 2014

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