Single Day of Quaint Road Tripping - Boston to NYC

The third week of October, I'm flying into Boston to toot around town for a few days while my husband attends a three day conference. Midway through the week we're renting a car and driving to NYC to visit my sister who lives in Manhattan. My husband really wants "big city time" since this will be his first visit to the big apple. I really want to get some quaint beautiful New England sights in on the drive and I'm having a hard time deciding which way to go. I know Abbots lobster would be a great place to stop but I'm just missing their season. Ideally we'd maybe catch some foliage, eat some local seafood, and just have a leisurely scenic drive. We'll go from spending one night in Boston to the next in NYC, per my husband's request. I'm more than willing because after he leaves, my sister and I are going to do our own trip out of the city (to The Mount in Lennox MA).
Any suggestions? Fun things that will stretch the drive?

Welcome aboard the RoadTrip America Forums!

You can certainly have a great, relaxed, scenic, and yes - 'quaint' drive from Boston down to New York if you can devote a full day to it. But you'll have to wend your way through or around the many urban centers that are in the way. Unfortunately, that means pretty much abandoning the coast and any traditional seaside lobster shacks such as Abbott's. So, while your husband is attending his business meetings, I suggest you get some seaside in by taking a Boston harbor cruise and that he take you for dinner one evening to a local Boston tradition, Legal Sea Foods. Both of those should be accessable by public transport or, at worst, a taxi ride.

Now, for your drive to New York. The good part is that late October is right around the peak of foliage season in this part of New England, so you're in for some great traditional views of New England in the fall. What I'd suggest is that you leave Boston via the Mass Pike (I-90) just to get out of town. Then take I-95/MA-128 north to MA-117 west. This will take you near the towns of Lexington and Concord, but if you want to see those, then MA-2 would be the better route west from MA-128 initially, but you will want to get back on MA-117. The next connection is a bit tricky, but it's typical New England. A few miles after crossing Boston's outer beltway, I-495, you'll take MA-70 south to the town of South Lancaster. There you'll bear right onto Sterling Road and follow that until it merges with MA-62 west. Continue on MA-62 to Barre MA where you'd pick up MA-122 around the northern end of the Quabbin Reservoir. At the north end of the Quabbin, you will hit US-202 and your navigation becomes a lot easier as you can just follow that all the way down to Danbury CT, and pick up I-84/I-684 down to White Plains and there pick your best route into the New York City, depending on exactly where in Manhattan your sister lives. Check with her on how best to get into the city.

All of that will take about eight hours of driving, but breaking it up with stops at roadside stands, to take pictures, walk in some of the many small New England towns you'll be passing through, and have lunch, you can easily spend ten to twelve hours from the time you leave your hotel in Boston until you arrive at your sister's. But it will be a thoroughly relaxed and enjoyable ten to twelve hours.

AZBuck

I recently spent the 4th of July weekend in Boston. What a great city -- partly because of the metro subway system. It's really easy to get around and see the sights at a walking pace.

Legal Seafood is a very good local chain -- I do have a recommendation for lunch in Boston's North End. Fantastic Italian restaurant -- great walking area -- and again I reached this using the subway system downtown. After eating -- check out the delis and ice cream shops -- a visual feast awaits you. Villa Francesca

The public art in the Boston Back Bay area is also a fun place to explore on foot. I was staying in a hotel in the Back Bay and so criscrossed that section of the city several times.

Mark