If we learned one thing from our first short day trip to Boston, it is that it’s great to have a local to show you around. We were ushered around Beantown by Chris’s knowledgeable and enthusiastic cousin, Emily. And even though she is an Annapolis, Maryland native, she has lived in and loved Boston for over five years. We got to see it through the eyes of someone who exuded rare vigor; the vigor of a person whose dreams were in the process of coming true. She was a wonderful hostess and managed to squire us to a ton of great places we definitely would not have found without her guidance.

But, if you don’t have a local to show you around, the good people of the internet are always at the ready and always updating the world with great advice and suggestions. So, in this article, we’re trying our best to provide vivid and useful details about our (albeit short) experience in Beantown.

We had one full day to hang out during our drive back to Philadelphia after visiting Maine, so we decided to skip the typical tourist attractions (museums, galleries, historical sites, etc.) and save those for a time when we could spend a little more time in the area. Instead, we aimed to fit in a solid day of hanging out with Emily while seeing new things that might be a little less on the beaten path.

Emily now lives in a suburb of the city and we opted to drive in town. As it turned out, the vehicle we were in definitely enhanced our Boston experience; Emily drives a Subaru. And I hafta say, it proved to be pretty easy to be a passenger, but Boston’s legendary drivers did not disappoint. We were cut off twice, which didn’t shake Emily one bit. We are also used to aggressive driving, but there is an added element of excitement when in a new city.

But, I digress. In the car ride, I learned that the basic layout of Boston has not changed much since it was first built, which is part of what makes its history so unique and inviting. Cart paths used during colonial times still map the majority of the city; they have since been paved and serve as the major routes for getting to and from heavily populated areas and centers of industry.

We parked in the Boston Common Garage, which is under Boston Commons. It’s not that amazing when you are in the parking garage (is it ever?), but when you walk on the manicured lawn of the park on top of it and stroll along the lovely, winding walking trails, it’s amazing to think that you are both on top of a parking garage and in the heart of the city. If you’re driving on a visit to Boston, I would highly recommend parking here. The rates are great and it gives you access to the whole city. Plus, if you get lost, it should be pretty easy to work your way back!

We arrived at lunchtime, and Emily had a plan. As she described it, we had plenty of options, but there was really only one choice. 🙂 The Parish Café and Bar was not only worth the inevitable (but not too long) wait, it was decidedly memorable and wow-worthy artisan food and beer. Even the menu at Parish is a work of art: it’s a compilation of several local chefs’ recipes from their own restaurants. Owner Gordon Wilcox created a list of the favorites of the Bostonian palate, making it the kind of place you absolutely must visit again. And, to wash down those delicious edible works of art, they keep a rotating craft beer list full of exciting flavors. Parish definitely made the shortlist of one of our favorite yum-spots we’ve checked out in the Northeast.

We walked off lunch through the theater district, eventually landing in a popular red-tented open-air restaurant called The Barking Crab (they think everyone should have crabs, heh). It sits right on the waterfront of the historic Fort Point Channel (where the Boston Tea Party took place!) Despite its serious history, the waterway made the setting relaxing and the red and yellow circus tent decor reminds you it is time to have fun. And, as an added bonus, a live guitar player/singer was entertaining the crowd when we visited.
Chris and Emily at the Barking Crab Chris and Emily at the Barking Crab
After enjoying another pint, we stopped by Quincy Market, a now-iconic building that I later learned helped add to the confusion of Boston’s streets. It was built in 1824 by known architect Alexander Parris. Its construction required the team to fill in part of Back Bay, then expand that area of town by adding six more streets. A trip upstairs in the building gives visitors a peek at the signs early vendors used to mark out their territory. South Market is another building added to the Faneuil Marketplace, which was restored to its 1826 appearance with the moneys from a HUD award.

Well, Chris and Sarah had become thoroughly confused by the streets, and we couldn’t even blame the beer. Locals, Emily told us, are fond of cheekily saying, “If you aren’t sure where you are, you shouldn’t be here.” The streets seemed to stop abruptly and turn with no warning, which was quite fine with Emily, who found our confusion amusing as she led us back to the car, which was really easy to find.
Even though we spent only a day there that time, we promised to make more trips back, and are both pretty pumped about learning more about the city. Have you been there? What do you recommend visitors do? What should we do next time we visit? Tell us about it in the comments!


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