Chicago -> Boston -> ?

We're going on an impromptu road trip and decided to head out from Chicago towards Boston. I haven't driven this far in some time so I have some questions.

How many hours should we drive each day? We'll be taking a Chevy Trailblazer by the way.

From Boston we can either go south to New York, but we've been there many times already. How is New England and what is there to see and do?

Should we book hotels in advance or just find one when needed?

Thanks for any help. We'll be leaving around the middle of March.

We're going on an impromptu road trip and decided to head out from Chicago towards Boston. I haven't driven this far in some time so I have some questions.

How many hours should we drive each day? We'll be taking a Chevy Trailblazer by the way.

From Boston we can either go south to New York, but we've been there many times already. How is New England and what is there to see and do? It seems like going north would be less hectic than congested New York.

Should we book hotels in advance or just find them when needed?

Thanks for any help. We'll be leaving around the middle of March and will have about 9 days to travel.

[Boston Wrangler]

C'mon down!

I've only ever used I-80/90 to get to/from Chicago. You can go up through Ontario, but that will make your trip a little bit longer. I have also heard the suggestion of taking I-86/88 through NY state instead of I-90. Although it's hillier and slightly longer, the scenery is much nicer and the traffic is lighter.

Once you're into the Albany area, you can pick up Route 2, which goes through the Berkshires and Taconic range in western Massachusetts and follows what is called the Mohawk Trail. There is some seriously good scenery and mountainous switchback roads. The drive from Williamstown (located in the northwest-most corner of Mass) to Boston is just about 3 hours, but you'll take longer because you'll want to stop for pictures and perhaps some souvenirs at one of the many traps along Route 2.

Do you plan on visiting Boston itself? You could spend all nine days in Boston and still be left with things to do and see. If you are in to history, you're coming to the right place. The revolutionary war started about 15 miles NW of Boston in Lexington. You can visit many national historical sites, take guided tours of battle sites and historic buildings in Lexington and Concord. In Boston you can follow the Freedom Trail, visit Quincy Market and Faneuil Hall marketplace.

There are whole books on things to do here. I could go on and on. If you tell us what types of activities and sights you are interested in, we can offer some more pointed suggestions!

Thanks for the reply. We'll definitely be taking I-80/90 to Boston but this Route 2 sound really interesting. We plan to stay in Boston for maybe 3 days or so. I'm a history major so I'm looking forward to seeing whatever historical sites I can. But for the sake of my brother, a science geek, what else is there to see? Fenway, Harvard (to gawk at our intellectual superiors), Boston Commons, Old Ironsides, Freedom Trail, and Faneuil Hall are on the list.

We're trying to keep the cost of this trip low so we'd probably avoid guided tours that aren't free, although we might make an exception for the Duck Tour which I have heard good things about. I'm just really wondering if Boston is a very walkable town? And is parking widely available or a pain to find? It looks like we'll be staying in the suburbs and driving into the city. Is there a major subway station with free parking that we could go to?

I'm not sure I've ever heard "Boston" and "free" in the same sentence. And you said "parking" too? Ha!

Seriously though, what suburb(s) are you thinking of staying in? I live ten miles from downtown up I-93. The concept of distance the Boston area is a lot different than most other places (i.e. 10 miles is "far"). You'll probably be best off leaving your car at the hotel (where parking is likely, get this... FREE!) and taking the hotel shuttle into town. Cab rides are fairly expensive in Boston compared to other metropolitan areas, but not too bad if you have 3 or 4 people to share the ride with. The subway system is pretty good, but not all that far-reaching into the suburbs. The commuter rail (purple line trains) go much farther from the city, but run less frequently.

Harvard isn't all it's cracked up to be. I went to Tufts and we have the distinction of being the only school in the country that looks down on Harvard. (Tufts is located on Walnut Hill in Medford/Somerville about 5 miles from Harvard.) Harvard Square is pretty good for walking around and the liberal/urban experience. You can get there easily on the Red Line of the subway system, which is known as "The T."

I'm a science geek too. The Boston Museum of Science is a great place to visit, and you can catch the Duck Tours right outside their building. Tours leave from the BMOS and the Prudential Center, which is more downtown. I took a Duck Tour and it was great! The Duck Tour is one of those things that I never thought I would do as a life-long Bostonian, but I really enjoyed it.

If you are going to follow the Freedom Trail, you'll see a lot of the city, and Boston is a very walkable city. Make sure you go to the North End and have some authentic italian cuisine and baked goods. I can recommend a bakery in the North End that isn't on Hanover Street (the main drag) that has baked goods that are just as good, if not better, than the overly famous Mike's Pastry.

I think we're going to stay at the Comfort Inn & Suites Logan located at 85 American Legion Hwy., Revere, Massachusetts 02151. From the reviews written on tripadvisor there apparently is a blue line T station (Revere Beach Station) a good 20-30 minute walk or short taxi ride away. Plus, there's free parking at the hotel. The only downside is that, according to reviews, this T station is in an "unsavory" neighborhood. But the hotel offers a shuttle to airport station as an alternative.

In the end, I think I was just being overly optomistic thinking I'd find parking easily :) It's just so much cheaper to stay out in the burbs. Our other hotel option is a place in Woburn but I don't think it's next to any T stations. It's located just north of Middlesex Fells Reservation on the highway.

[Boston Wrangler]

I would spend a few extra dollars and stay somewhere other than Woburn, which one of those Commuter Train stations that I mentioned. There is a Courtyard by Marriot on Mishawum Road in Woburn that is pretty close to that train station.

There's an Amerisuites in Medford, MA, which is closer to Boston than Woburn, and more savory than Revere. I bet that the Amerisquites has a shuttle to Davis Square Somerville where you can pick up the Red Line, which is much more savory than the Blue Line.

There's also a Tage Inn (now a La Quinta I believe) right next to I-93 in Somerville. That hotel is about 1 mile from the Sullivan Square stop on the Orangle Line, which is less savory than the Red Line, but still more savory than the Blue Line. That La Quinta is also in a more savory neighborhood than the Revere Comfort Inn.

Revere Beach is cool though. You definitely have to go to Kelly's Famous Roast Beef http://www.kellysroastbeef.com . They are Boston landmark on the beach that has take-out windows only and they're open 24 hours a day 364 days a year. They're also know for great seafood, and in my opinion, their onion rings are the standard upon which all other onion rings are to be judged.

My replies are getting a bit long-winded, so feel free to email me at the address I have listed above and I'll give you plenty more local info! I'm sure we can find you a place somewhere savory AND close to a T station.

Your long-winded replies are much appreciated. I booked a room at the La Quinta (a.k.a. Tage Inn) that you suggested. It got rave reviews on tripadvisor and is much closer to everything. Plus, it was only $15 more per night. Thanks for all the help... I can't wait to get there.

[Boston Wrangler]

Sounds great! Still feel free to email me and we talk more specifics if you'd like. Good luck!

I'd like to make a correction to one of my posts above. I meant to say that I would spend a few dollars and stay somewhere other than Revere. Sorry for any confusion, but I'm sure you'll like the proximity of the La Quinta!

I suppose I have just one more question. How realistic would it be to leave Chicago in the afternoon, drive overnight, and arrive in Boston the next morning? There would be two people driving and we could both take shifts. We want to get there quickly and without having to spend money on a stopover motel on the highway.

Plan B would be an early morning start from Chicago to Syracuse. Then, take a 4.5 hour drive early the next morning to Boston.

So would you advise stopping or gunning it? As I stated in my first post, I haven't driven this far in a long time so I could just be thinking optimistically when I say that we can do an overnight trip.