Boston and surrounding area trip

[Passepartout]

Thankfully, we are not planning on having a car while in Boston. Just for the road trip prior to our week at Custom House.

I am considering expanding our road trip a couple of days so we won’t be rushed. We will lose a day to travel the day we arrive. We will be using miles, and the Alaska flight would get in around 5:40 PM. I don’t want to set out in the dark on unknown roads during rush hour. Especially since I’m the navigator.

Thanks to all for your very helpful advice!

A couple of points, you are coming from the West coast, so 5:40 Eastern time is just 2:40 'body time'. And there is about a 99% chance that your rental car will have Apple Auto and/or Android Auto. The navigation will be handled by your smart phone and you'll see it on the car's big screen.

 

[sun starved Gayle]

That's exactly what my husband said ! Funny.

 

[Big Matt]

I strongly recommend a trip to Cape Cod and Martha's Vineyard. MV is an easy day trip. One thing to note is that things start to shut down the week after Columbus Day in parts of the Cape and MV. You may also enjoy things south at Duxbury or north at Marblehead .

 

[ambere]

We just got back from a trip to New England, including Boston, Cape Code and Martha's Vineyard. We really LOVED Martha's Vineyard; wish we could have stayed longer. Newport, RI is a great day trip from Boston, too.

 

[rapmarks]

Literally anywhere. You can get from Logan to 90% of everything interesting without worrying about driving and ESPECIALLY parking. Parking is a nightmare. The world's most expensive parking spot was auctioned off in Boston, after all. There's really no down side -- cheaper, faster, and considerably less hassle.

Then take a commuter train to Gloucester or similar and rent a car there to look at leaves. Boston is CONSIDERABLY less fun behind the wheel of a car.

Bringing back horrible memories of driving in Boston, constantly getting on wrong roads, so lost.

 

[ScoopKona]

Bringing back horrible memories of driving in Boston, constantly getting on wrong roads, so lost.

It's a wicked p*ssah.

 

[klpca]

We travel to Boston a lot, mostly early to mid-October, and stay at Custom House.
We've been 9 times in the last 13 years, and only missed a few because of the pandemic.
We've done many fantastic out-trips, all taking the better part of a day---
to Lexington & Concord (towns and battlefields/historic);
a bus tour to Newport RI to see the many famous mansions (Vanderbilts had two on tour: Breakers and Marble House), and to spend the day walking around Newport;
to Ogunquit ME (great shops and cafes, and the glorious walk along the magnificent spectacular shore, called the Marginal Way);
through the countryside just to see the foliage; stopping at an outdoor produce/apple cider market;
and visiting many other historical places around the Boston area like Waldens Pond,
Sleepy Hollow Cemetery (and the specific area there where many, many famous authors are buried----Author's Ridge).

One time, back in 2019, we rented a car and drove up to Vermont for a few nights and then to New Hampshire for a few more nights....
the foliage was peaking at both places we went (by design as we traveled to NH after VT, and the peak followed us).
We drove the famous Kancamagus Highway, and it was jaw-dropping.

In Boston, there's more to do than you can imagine, and around town the "T" will get you there cheaply and easily.
The Boston Museum of Fine Arts is fantastic. The Harvard campus is beautiful & fascinating. Great architecture. Bookstore alone is great!
Back Bay and the cobbled stone streets of Beacon Hill are a must!
Even the nearby Boston Market is amazing---produce, flowers, etc.

Google "Things to do in and around Boston" and also visit the concierge as soon as you get there.
You may even get a full list of bus day tours (and book one or two) prior to going so that the special tour you want isn't already booked.
I also highly recommend doing the city bus tour which leaves just off Atlantic Street in front of the Marriott Long Wharf Hotel & near the Aquarium.
We neglected to do that for at least 6 years, but now we do that at least twice a day when we're there. It looked "touristy" at first but we were truly missing out on a treat.
It's relaxing just to sit and listen, and each tour guide is totally different, and the places you see and the things you learn are NOT in books----absolutely fascinating.

We are returning to our "favorite big city" this upcoming October again, and can't wait.
We love walking to dinner each evening somewhere in the North End ....that's our favorite activity!
We stop in at Modern Pastry (on Hanover Street) way too much ---- it's the best! I also have a great restaurant list for Boston.

BTW, two of our trips in early December, just to experience the Christmas season, and that was so memorable......
Spontaneous musical groups at Faneuil Hall and Quincy Market each day/evening, and the famous huge Christmas Tree is spectacular.
The crowd even joins in on the carols.
Great shopping all over...... and we also attended the Christmas Holiday Pops concert....WOW!
Boston can be cold during Nov/Dec but we just bundled up and went just as in October---it never slowed us down one bit....
even continued our walks to North End for dinner each evening. Some amazing food there..........

P.S. Confession of our secret....Shhhhhhhhh.......We truly love Boston because we can just FEEL the presence of SueDonJ .....

Thanks for this information. We are headed there just after Thanksgiving. I'm not sure if the Christmas decorations will be up yet but we'll see when we get there. We are prepared to bundle up. After spending a lot of time in Truckee last winter, my attitude about the cold has changed. 10 degrees was cold. 30 felt balmy by comparison. We walked outside almost every day so we feel like we can handle cold temps in Boston. Do you have any other winter tips?

 

[rboesl]

expand...

"Bringing back horrible memories of driving in Boston, constantly getting on wrong roads, so lost."

Our son went to Boston University so we did our fair share of driving there. So far the city of Boston is the only place where I have driven in which making 4 right hand turns consistently does not get you back where you started.

 

[ScoopKona]

So far the city of Boston is the only place where I have driven in which making 4 right hand turns consistently does not get you back where you started.

But if you were hoping to visit Waltham -- the exact opposite direction of BU -- it's just perfect.

There are a few cities I absolutely refuse to drive -- Cairo, Rome and Boston. It's not that I don't drive there. I won't drive there. I wouldn't do it if someone was offering $1,000 per hour to do so. Thanks, no. I'd rather have a root canal.

 

[sue1947]

But if you were hoping to visit Waltham -- the exact opposite direction of BU -- it's just perfect.

There are a few cities I absolutely refuse to drive -- Cairo, Rome and Boston. It's not that I don't drive there. I won't drive there. I wouldn't do it if someone was offering $1,000 per hour to do so. Thanks, no. I'd rather have a root canal.

Bringing back horrible memories of driving in Boston, constantly getting on wrong roads, so lost.

Years ago, when I first visited Boston (probably '70s), I read the following (paraphrased after all these years) and found it to be true:
Boston roads used to be 17th century cow paths and only a 17th century cow can understand them.

 

[TheTimeTraveler]

Bringing back horrible memories of driving in Boston, constantly getting on wrong roads, so lost.

I don't encourage anyone to drive in the Boston area unless they are actually from Boston.

I grew up in Boston, and when I go back to visit even I am not happy driving in or around Boston or it's circumferential highway which used to be known as Route 128 (nowadays they call it Route 95). And Route 128 truly isn't circumferential as you run into the ocean on both ends of it.......





.

 

[nerodog]

You can drive up through some of North Shore as mentioned from Boston and ho to Maine coastal route up to Freeport and on to Acadia. No car needed in Boston. That way your husband would focus on his highlights.. Ogunquit and Kennebunkport are nice as well as Rockport and Camden, Boothbay area. Rather than try to go to every state I'd focus on Maine and Boston..Marblehead, Newburyport, Rockport. I'd also suggest York Harbor in Maine and go to Stonewall kitchen.

 

[dago]

.

I too grew up in the Boston area, and I can attest to the traffic nightmare. I haven't been back to that area in over 40 years. That's the 1 thing I do not miss about Boston.

As for the rest of the road trip... As others have said Coumbus day weekend is very crowded. The fall foliage in VT and NH is excellent at that time of year. I would strongly recommend having reservations if you are planning more than 1 day.

Fifty years ago, when we were newlyweds and living in MA, we decided to take an impromptu trip to VT and NH for the fall foliage. It just so happens that it was indeed Columbus Day weekend. We had not made any reservations. It was an adventure. There was little available lodging. We lucked out and found some people that were willing to take us into their home for a nite (not something I would be comfortable with in today's environment). Next day we continued on and found a place that had a vacancy. By happenstance, a motel had a cancellation, and a room became available. Needless to say, it was rather stressful and we vowed never to do it that way again. The good news was that we enjoyed the scenery and got to see a lot of places. We were not too far from home (maybe 3 to 4 hours), so if we got shutout, it wasn't a big deal to drive back home.
BUT, not well thought out.

 

[WaikikiFirst]

grew up in Boston, and when I go back to visit even I am not happy driving in or around Boston or it's circumferential highway which used to be known as Route 128 (nowadays they call it Route 95)

I grew up there, lived there for almost 40 yrs. If they now call Rt 128 "Rt 95" (which it always was) I ain't ever going back.
Next they'll be naming Boston Garden after some bank or something.

 

[dago]

I grew up there, lived there for almost 40 yrs. If they now call Rt 128 "Rt 95" (which it always was) I ain't ever going back.
Next they'll be naming Boston Garden after some bank or something.

I grew up and lived there 32 years. Boston Garden is no more. Demolished in 1998. New home for the Bruins and Celtics is TD Garden (FKA The Fleet Center). Indeed, named after some bank.

 

[WinniWoman]

I too grew up in the Boston area, and I can attest to the traffic nightmare. I haven't been back to that area in over 40 years. That's the 1 thing I do not miss about Boston.

As for the rest of the road trip... As others have said Coumbus day weekend is very crowded. The fall foliage in VT and NH is excellent at that time of year. I would strongly recommend having reservations if you are planning more than 1 day.

Fifty years ago, when we were newlyweds and living in MA, we decided to take an impromptu trip to VT and NH for the fall foliage. It just so happens that it was indeed Columbus Day weekend. We had not made any reservations. It was an adventure. There was little available lodging. We lucked out and found some people that were willing to take us into their home for a nite (not something I would be comfortable with in today's environment). Next day we continued on and found a place that had a vacancy. By happenstance, a motel had a cancellation, and a room became available. Needless to say, it was rather stressful and we vowed never to do it that way again. The good news was that we enjoyed the scenery and got to see a lot of places. We were not too far from home (maybe 3 to 4 hours), so if we got shutout, it wasn't a big deal to drive back home.
BUT, not well thought out.

And be I prepared for lots of traffic in VT sbdcNH also!

 

[ScoopKona]

Next they'll be naming Boston Garden after some bank or something.

I'm looking forward to Prudential Stadium, the home of the Prudential New England Red Sox.

 

[WaikikiFirst]

I almost wrote something about Fenway. You made me look for whether somthing had been announced about a name-branding. Gullible me.
The one that got me was when I went to Kenmore Sq in, idk, maybe 2005, and one of the things I wanted to do was go into "The Rat". Well, The Rat had been replaced with a trendy boutique hotel for helicopter moms of BU students and prob a few Fenway-mecca tourists.

 

[silentg]

We are originally from Boston. Moved to Florida in 87. Still here, but visit Massachusetts where most of the family live. Enjoy the summers up there hope to spend more time there. Going to visit Cape in October.
Boston is very busy and crowed. You will have more fun exploring other parts of the state. Also Maine and New Hampshire are beautiful in the fall. Have a great time.

 

[dago]

We are originally from Boston. Moved to Florida in 87. Still here, but visit Massachusetts where most of the family live. Enjoy the summers up there hope to spend more time there. Going to visit Cape in October.
Boston is very busy and crowed. You will have more fun exploring other parts of the state. Also Maine and New Hampshire are beautiful in the fall. Have a great time.

October is a nice time to visit the Cape.

 

[nerodog]

October is a nice time to visit the Cape.

Totally agree..
A beautiful month in New England.

 

[Myrtle]

I remember a trip to Boston with my Denver,CO born huIsband. I booked the car rental, and at that time the exit was to Callahan Tunnel to get the Expressway south. Traffic was a crazy, and we were getting pushed aside over and over trying to enter the expressway South. Finally at a standstill - Being from Mass, --- I rolled down the window and the net guy beside me , in the very fancy car saw my girl wave, and opened the passenger window. I Yelled; buddy, this is a RENTAL!...he nearly fainted, and conceded we were on our way south!

 

[dago]

As I said I am originally from Boston, so I am used to traffic jams and rush hour. As bad as everyone is making it out to be, the Boston traffic is a breeze compared to Chicago.

 

[silentg]

As I said I am originally from Boston, so I am used to traffic jams and rush hour. As bad as everyone is making it out to be, the Boston traffic is a breeze compared to Chicago.

I’ve never been to Chicago, but I thought DC traffic was worse than Boston.

 

[dago]

I’ve never been to Chicago, but I thought DC traffic was worse than Boston.

I lived in the DC area for 3 years back in the late 60's early 70's. I agree, DC traffic was worse than Boston, but for me still tolerable. I never lived in Chicago but driven through the area many times and no matter what time of day it was, traffic was heavy. My son complains about Atlanta. He has gotten caught in some massive traffic jams every time he's gone through there. He has no problem with the Boston situation.