Boston Freedom Trail Tips?

Senator

Thinks s/he gets paid by the post
Joined
Feb 13, 2014
Messages
3,925
Location
Williston, FL
I will be headed to Massachusetts in November 2-9 for a HS reunion. While I am there, I would like to go on the Boston Freedom Trail. I know there are many tours, and I can go by myself.

I typically like a tour guide, as I learn more. It's been a long time since I lived there, and generally stayed away from Boston.

I will be staying in Middleboro, about 45-50 miles from Boston. I have a rental car. I would guess traffic is a nightmare? Parking non-existent?

Any tips on pursuing the Boston Freedom Trail? A good tour company? Best way to get to Boston from Middleboro (and back). I have a day. How many hours, at a minimum, should I plan?
 
DW and I were there Memorial Day Weekend, and opted for a guided tour with Freedom Trail Foundation The Freedom Trail Our guide was knowledgeable, funny (she and I competed to come up with more puns) and kept it interesting throughout. Highly recommended.
Traffic can be difficult so allow for sufficient travel time. Parking was not an issue; we were there on a holiday weekend, so I don't recall if on-street parking is restricted Monday to Friday. But garages are available.
If available, also consider the ghosts and gravestones tour www.ghostsandgravestones.com. Lots of fun.

Union Oyster House is supposed to be a must-visit for dinner. Your taste may differ of course, but DW and I were unimpressed.
 
We just did the Freedom Trail a couple of weeks ago. Stayed in Lexington - took the subway into Boston. Had a great time on the Freedom trail. Took 2 guided tours - 1.5 hrs each. First one went from Boston Common to about the middle of the trail. Then the 2nd to the north. Guided tour ended and we went solo across the Charlestown Bridge to the USS Constitution.

Tour Co we took was Tour of the Freedom Trail Boston's Best Tour located in a standalone building in Boston Common by the Park St MTBA station. We didn't pre-register. We just walked up at around 10:30 and got in the 11 am tour, and then the 1:30 farther north. Tim our tour guide was very knowledgable and entertaining.

After the US Constitution, we walked back to Boston Common, stopping for dinner at the Union Oyster House - oldest restaurant in the US. Took the subway back to Alewife train station parking deck and drove to our hotel. A fun day - (probably 9:30 am to 8:00 pm)


OP - I would plan on spending the whole day along the trail. And download a MTBA map to find the nearest train station to your hotel. Drive to the train station and take the train to the Park St Station.

Have a great time!
 
FT was great. DW & I did on own some 7-8 years ago. Love going thru old cemeteries & looking at gravestones.

I'd go to Quincy to see John Adams birthplace plus JA & JQA home & burial site.
 
Went out to east coast with camper in Sept. Took subway, I believe it was out of Alewife, that took us to Park St. At subway exit you are across from Boston Commons. There is a Visitor Center right there to get a trail map and can sign up for a guided walking tour. Not sure what they all tour.
At first I was going to walk the trail with a map but felt we would not get it all in a day especially if you want to get to the US Constitution at Navy Pier.
The visitor center also sells tickets to the On Off Trolley and this is the way we toured. You can get on the trolley a half block from the visitor center. You can get on off and on again at any one of their stops.
The drivers are very informed and share a lot of information on the many places they pass and they give it a personal note because they are local. The trolley cost included a harbor boat tour. We got off there and were able to board the boat with in a half hour. While out in the harbor they informed us they would be stopping at the Navy Pier for a brief stop and anyone wanting to get off had the opportunity. Knowing that a trolley stop was close to the pier we got off and toured the destroyer and the US Constitution. From that point we got off at the original State House admission was also included in trolley price. From there we walked to the cemetery and back to Boston Commons. This really worked well for us and even with the trolley we did a lot of walking and didn't see all we wanted.
The locals are very helpful. Couple of times when they saw us studying the map they stopped and offered assistance.
When returning to Alewife the subway was full and had to stand but as it continues out of the city more passengers get off. Coming into the city Alewife is the first station so seating was not an issue. The worst was hitting both the AM and PM rush hour when driving from and to the campground.
Just another option. There are also trains and busses that go into Boston but I would do the subway again. They say Boston is walking friendly.
Felt safe the whole time there. Steve
 
The Freedom Trail runs through Little Italy. Many good restaurants and tourist-trap restaurants there. The tourist trap ones are right ON the Freedom Trail.

If you're hungry, peer down an adjacent street (to the Freedom Trail) looking for an Italian restaurant that the locals likely frequent. Better food at much better prices....and just a few steps away from the FT. These often seemed to offer early-bird dining specials, too...which might let you miss riding on a crowded rush-hour subway back to your car/hotel.

-----

There's a fierce cannoli competition between 2 bakeries in Little Italy -- Mike's and Modern. I liked them both. https://www.pratesiliving.com/cannoli-wars-mikes-pastry-vs-modern-pastry-boston-ma/

-----

The On/Off trolley with harbor boat tour is a good deal, too.

Wear comfy shoes and have fun!

omni
 
As an engineer? You may enjoy looking up the Boston Museum of Science. Eating in the snack bar you over look the Charles River with MIT and Harvard in the distance, and that portion is free! The Omni Theater is narrated by Leonard Nemo (spock) who grew up around the corner from the museum.

Another good museum is MIT, which would be a short cab ride from the Museum of Science. Though I've never been I passed it all the time while calling upon the University.

Take a ride on the famous ducks in the park, then take a 8 block stroll from the park down Newbury street (very artsy shops), and finish it off 1 block south at the Prudential Tower Top of the Hub restaurant with a cocktail and appetizer. I don't recommend the dinner it is pricey and the last time I was there thought it was under whelming. Drinks will be pricey $10-$15, but the view is awesome!

Not freedom trail related, but the back bay area is pretty cool.

https://www.google.com/maps/place/N...534479f63150bf!8m2!3d42.3492917!4d-71.0836492
 
The Freedom Trail runs through Little Italy.

There's a fierce cannoli competition between 2 bakeries in Little Italy -- Mike's and Modern. I liked them both. https://www.pratesiliving.com/cannoli-wars-mikes-pastry-vs-modern-pastry-boston-ma/

omni

We call it the North End around here. Mike's is my favorite when it comes to canolis.

To the OP the MBTA train from Middleboro to South Station is your best option. You will be a couple of blocks from the Common but if you decide to drive allow 1.5 hours from Middleboro with traffic. Plenty of parking garages around.
 
Last edited:
I went to Mike's a couple of weeks ago. I have never seen anything quite like that place. A half hour long line for pastries in the late afternoon? It was well worth the wait.
 
We call it the North End around here.

And Wednesday, in the North End of Boston, is Prince spaghetti day!!:dance:

Sorry, a blast from the past.:D

The original Regina's Pizzaria used to be there (much better than the one in Quincy market), and there was an out of the way place called the Pushcart with great lasagna. These are 40 year old memories, so the places may have changed.
 
I will be headed to Massachusetts in November 2-9 for a HS reunion. While I am there, I would like to go on the Boston Freedom Trail. I know there are many tours, and I can go by myself.

I typically like a tour guide, as I learn more. It's been a long time since I lived there, and generally stayed away from Boston.

I will be staying in Middleboro, about 45-50 miles from Boston. I have a rental car. I would guess traffic is a nightmare? Parking non-existent?

Any tips on pursuing the Boston Freedom Trail? A good tour company? Best way to get to Boston from Middleboro (and back). I have a day. How many hours, at a minimum, should I plan?

Hi Senator, congrats on your retirement! I grew up nearby to Middleboro, and would definitely recommend taking the commuter rail to South Station from Middleboro- much easier than driving... From SS, you can go to the SS subway station and go to the appropriate stop to meet your tour operator (if not walking distance from SS). Weather in early November could be iffy for an outdoor walking tour. If weather s lousy, perhaps consider a Duck Tour- they are also a fun way to see the city. Another good tour to consider is a foodie tour if the weather is good. I've done one in the North End which was excellent. Regarding FT- I've never personally done one, but would suggest a Trip Advisor search for reviews on possible operators. Hope you enjoy your trip and reunion!
 
Back
Top Bottom