Upcoming Boston Trip

I lived in the Boston area for 5 years after college before moving back to the midwest a couple of years ago. Here are some of my suggestions:

-If you've never been to Boston you've got to do the Freedom Trail. Start in the Boston Commons and plan for a day at your own pace. For a good break, stop at the Bell in Hand Tavern before heading over to Modern Pastry in the North End. Bell in Hand is a great place to rest and grab some food/drink partway through the trail stops.

-For dinner and a great skyline view, check out Pier 6 over by the Charlestown Navy Yard.

-Get a Charlie Card and ride the red line over to the Kendall Station to see MIT and Harvard Station to see Harvard Yard.

-For ice cream check out J.P. Licks. There are multiple locations, but we always like the Harvard Square spot.

-For more American history, venture a bit out of town to the Lexington and Concord area. Go to the Minuteman National Historic Park visitor center (great movie every 30min) and then walk a bit of the battle road. If you have time, drive in to Concord from the visitor center and see the Old North Bridge where the 'shot heard round the world' occurred.

-Sam Adams is a good tour, but I really liked taking friends to Harpoon Brewery. They have a tour and a great beer hall atmosphere.

-Visit Castle Island to overlook the Boston harbor ship traffic and planes landing at Logan airport and eat at Sullivan's. Then walk around 2 mile path around Pleasure Bay. You'll likely hear some real Boston accents here.

-The JFK Library and Museum is really great too.

Have fun! Fall is great in the northeast!
 
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Make sure to check out the Boston Tea Party Museum! It's very interactive and lot of fun.

I really enjoyed Salem (and it's gonna be beautiful in late October, if not a little crazy since they lean into the whole witch theme).

If you can, head down to Plymouth for an a day. The town is really quaint, and there's also the Plimoth Patuxent Museum. It has a recreation of the Pilgrims village and a local Patuxent tribe village. There's also the Mayflower II. And for food, you can't go wrong with The Lobster Hut and Cupcake Charlie's!

If you have a free evening, try candlepin bowling. It's a lot of fun, and something that is uniquely New England. The Simpsons featured it in their "The Town" episode --- Candlepin Bowling.

The Old North Church is a must see. Also, just up the street is the Skinny House!

If you can, take a graveyards tour. There are so many famous people who are buried in Boston.

For book lovers, check out the Boston Public Library, and the Boston Athanaeum, one of the oldest private libraries in the U.S.!
 
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As another person who lived out there for a handful of years,

- A couple of expensive but tasty places to grab seafood are The Barking Crab and James Hook & Co

- our favorite place to eat in the North End was Giacomo’s. It is not the kind of Italian place where you sit and people watch all night, you’re in and out. But the food is good. Fair warning, it gets insanely busy and it’s cash only. No reservations.
Outside the North End my favorite Italian place was Olivia’s Bistro in Newton.

- For a fancy night out, La Voile on Newbury Street is great. Otherwise Newbury is sort of fun to just wander down with a lot of very bougie shops.

- As others have mentioned, The Freedom Trail is great particularly if you’re interested in history

- Symphony Hall is a world-class concert hall if that were up anyone’s alley

- Downeast Cider House for good unique cider

- For museums, both the Museum of Fine Art and the Isabella Stewart Gardner Museum are really good, and those two can easily take up your day. There’s also a Museum of Science attached to MIT’s campus that should be re-opened by now after moving a couple years ago to Kendall Square

If you’re planning on using public transit (“the T”), I recommend the Transit app. It’ll give you arrival times for subway, bus, and commuter rail. Note that you use Charlie Cards or Charlie Tickets to pay for bus and subway, but there’s a separate system to pay for the commuter rail, if you were going somewhere further.
 
I spent the night down there a lifetime ago. Slept on the street.

Looking back I'm not sure what in the holy hell we were thinking.
Yah you're lucky you lived through that.
Mine was a post college business trip in the 80s. Bunch of dumb Midwest kids that thought we couldn't get hurt. Two nights of it and didn't get into trouble. But man, those strip clubs. Unbelievable.
 
Worse than LA?
Boston has the nicest people. friendly, smart, and even helpful...but once in a vehicle they are not the same and the city is difficult to navigate (DC is close).

DON"T DRIVE in Boston is not just advice it is a survival guide. Take the rails. There is so much history in that town it's hard for me to pick out a few so do what sounds most interesting to you...Freedom Trail is a great start though.
 

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