For food, go to the North End (Italian) and the Back Bay for everything else. Cambridge has some great little bars for hanging out, music (blues and jazz if that's your thing), and great atmosphere.
For some good hiking, go to Sunapee State Park in New Hampshire. Very small town but definitely away from it all after spending time in Boston.
I am from Connecticut, love New England and I still consider it home. I also lived in England (East Anglia) for some time.
If you like the outdoors, New England is a paradise, regardless of the season. If you like touring, New England is a paradise. If you like scenery, New England is a paradise. And although there are some unique problems with living in New England, the region's six states (actually five states and a Commonwealth) boast some of the highest quality of life indexes in the US, along with per capita incomes to match.
For the bad:
1. You must be careful in outdoor activities especially in Southern New England. Lyme disease is named for Old Lyme, a town in CT. Deer have multiplied without natural predators to become pests and deer ticks do carry Lyme disease.
2. Traffic on I-95 is horrible and it is like that from Boston all the way down to New York. Same as I-91 from New Haven CT through Springfield MA. And I-93 in Boston is a mess with the Big Dig. I would recommend alternate routes.
For the good:
Providence: Down I-95 from Boston. Providence is the capital city and the downtown area is becoming rapidly gentrified as the Boston Transit Authority commuter rail now leaves from Providence, making the city literally a Boston suburb. Ivy league schools,
Newport: One of the US's grand dame towns -- take a drive down the Ocean Drive and see some of the largest and most sumptuos mansions and castles ever built in the continent. Many are open to the public. Lots of history -- 17th century Quaker meeting houses, the oldest synagogue in the US, and of course, the NEwport Jazz Festival. You can also take a ferry to Block Island from Newport. Delightful town
Beaches: Some that are very good. Misquamicut is near I-95 and with easy access.
Mystic Seaport: 17th century whaling port totally restored to functionality. Almost accross the border with Rhode Island
Foxwoods: Nearby Mystic. Site of the wealthiest native american tribe in the US, thanks to a giant casino. Although I do not gamble, the place is worth a visit.
New London: Nuclear Sub base and site of the US Coast Guard Academy
Fairfield County: Not much to see on the way to New York. High traffic, industrial, lots of money, and lots of attitude from people.
Old Sturbridge Village: Re-creation of a Puritan village. Worth seeing. Just right off I-84 over the Connecticut border into Mass. before the Mass Thruway.
Tanglewood: The summer place for the Boston Pops and the Symphony Orchestra. Spectacular scenery in the Berkshire Mountains and one of the oldest settled areas in the US. The area has beautiful villages, very typical New England. Very folksy, progressive people.
Boston: JimK and Roy already told you about it. There is a Boston Heritage trail that walks you through the historical part of Boston. More US history concentrated in Boston than probably anywhere in the US. Outside Boston, Marblehead is an absolutely gorgeous town with artists, folk singers, etc.
Vermont: The entire state is a post card. Very green -- in more ways than one. Billboards are banned, outdoor commercial advertisement is severely restricted, and environmental laws are strongly enforced. As a result, it enjoys about the highest quality of life in the US. Instead of taking I-95, I would recommend Route 7 through Bennington, Arlington, and Manchester all the way up to Burlington. Side detours through Killington are also spectacular.
New Hampshire: I-93 from Boston takes you through the White Mountains. More spectacular views. Excellent hiking and over 40 4-thousand foot mountains in the place.
Maine: Just a hop away. Old seaside whaling villages, very picturesque. Kennebunkport and Oqunquit are two of the nearest villages to Mass. Shopping mecca at Freeport, with LLBean and many other outfitters having their headquarters there. Acadia and Baxter national parks also worth a visit. Castine is also in my memory as one of the most beautiful seaside villages I've ever seen.
Hope this helps.
Out of the way places: Block Island is absolutely gorgeous. Not as commercialized as Nantucket. Sandy beaches, farmland left, and rocky bluffs that could remind you of Dover England. Lots of bicycling, nature stuff, and the island has rare birds and endangered species still there. Definitely a change of pace.
[This message has been edited by lbotta (edited 07-31-2001).]