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.

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.

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.

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.

I have driven from Boston to Indianapolis in one day (I did all 1000 miles of the driving, but someone else was in the car with me), so I consider Chicago to Boston in one day very doable with two drivers. I would advise you to stay on I-90 through Massachusetts rather than get on Route 2 for the scenic drive, though.

If you want to shotgun-it here, my suggestion would be to leave Chicago early in the morning after a solid 8-hour sleep, drive all day, arrive at your hotel, get something to eat, settle in for the night, and be bright-eyed and bushy-tailed to grab Boston by the reigns the following morning. If you drive overnight, you're just going to want to sleep-in in the morning, which won't make the most of your time here.

Personally I like driving at overnight because there is hardly anyone on the road besides truckers, and I have a CB in my car, so I can always strike up a conversation with the truckers anyhow. There's something about the sound of a turbodiesel spooling up at 2 A.M. that I love. =)

I'm surprised you didn't mention Durgin Park...though that atmosphere may not be for everyone. Walking around the North End for a place to eat, you can't go wrong. And as a rub to Darrel, most Bostonians think "Boston-128-California" ;-) I guess it's a good thing they have the Red Sox!

What day are you planning on leaving? Sunday night on the Pike is not the best day, even out in the boondocks of Western MA. If you get the chance, don't miss MA route 2, at least the section from NY State line to I-91. I find that to be the most enjoyable stretch of highway, as after that it gets congested. MA route 9 from NY line is nice as well. Basically anything West of I-91 is a good choice, with my choices being 2,23,9, and US-20.

I-90 in NY seems to take forever, though it is a much better option than the (partially non-existent) Southern Tier Expressway of I-86/88, which actually does take forever. I work with a former long-haul trucker, he said that sometimes going through PA was quicker...strange.

As for a turbodiesel at 2am...I admit it, that's another reason I bought my TDI, I always loved hearing that sound of a big Cummins engine spooling up. Now I get to emulate it --end corny statement--

Hope your trip is a great one!

Ah, Durgin Park. Yes, but I did mention Quincy Market and the Faneuil Hall area, which Durgin Park is technically a part of.

Guy, you should also play a few strings of candlepin bowling while you're here or maybe check out how the Mass Ave bidge is measured in "Smoots."

Anyone from outside of 128 is a tourist as far as we're concerned! Part of Route 128 is also I-95. Part of Route 128 South is also I-93 North. Confused yet? We've got plenty more for you when you get here! :)

Albeit I don't drive an oil-burner like you Timbo, but the turbo in my WRX wagon engine makes good spooling audio :)

Here's some content from http://www.masshole.com that I love.

When we say = We mean....

bzah = odd
flahwiz = roses, etc.
hahpahst = 30 minutes after the hour
Hahwahya? = How are you?
khakis = what we staht the cah with
pissa = superb
retahded = silly
shuah = of course
wikkid = extremely
yiz = you, plural


How we'll know you weren't bon heah:

You wear a Harvard sweatshirt.
You cross at a crosswalk.
You ask directions to "Cheers."
You order a grinder and a soda.
You follow soccer.
You eat at Durgin Park.
You pronounce it "Worchester."
You walk the Freedom Trail.
You call it "Copely" Square.
You go to BU.

Getting around:

Boston is a mishmosh of 17th-century cow paths and 19th-century landfill penned in by water. You know, "One if by land, two if by sea." Charlestown? Cahn't get theyah from heah. And which Warren Street do you want? We have three plus three Warren Avenues, three Warren Squares, a Warren Park, and a Warren Place. Pay no attention to the street names. There's no school on School Street, no court on Court street, no dock on Dock Square, no water on Water Street. Back Bay streets are in alphabetical odda. Arlington, Berkeley, Clarendon, Dartmouth. So are South Boston streets: A, B, C, D. If the streets are named after trees (Walnut,Chestnut,Cedar,)you're on Beacon Hill. If they're named after poets, you're in Wellesley. Dot is Dorchester, Rozzie is Roslindale, JP is Jamaica Plain. Readville doesn't exist.


The North-East-South-West thing:

Southie is South Boston. The South End is the South End. The North End is east of the West End. The West End is no more. A guy named Rappaport got rid of it one night. Eastie is East Boston. The East End is Boston Harbor.


About our "cuisine:"

Boston cream pie is a cake.
Frappes have ice cream; milk shakes don't.
Chowdah does not come with tomatoes.
Soda is club soda. Pop is Dad. If it's fizzy and flavored, it's tonic.
When we mean tonic water, we say tonic water.
Scrod is whatever they tell you it is, usually fish.
If you paid more than $6 a pound,you got scrod.
It ain't a water fountain, it's a bubblah.
Brown bread comes in a can. You open both ends, push it out, heat it and eat it with baked beans.
They're hot dogs. Franks were people who lived in France in the ninth century.