A Christmas Season Visit to Boston | City Sidewalks, Busy Sidewalks

Whether the goal is shopping, dining, seeing a show, or taking in the sights, a visit to Boston during the holiday season is a great way to put yourself in the Christmas spirit. Many folks head in for a day-trip each December, but if you’re lucky enough to squeeze in an overnight or a weekend stay, you’ll be able to double your fun. While downtown Boston offers a collection of legendary fine hotels, if the parking woes and high room rates have you running for the hills, it may benefit you to set your sights slightly outside the city. I recently visited Boston as a guest of the Holiday Inn Boston-Bunker Hill in the neighboring city of Somerville, MA. Located less than 2 miles from downtown Boston, the Holiday Inn (could there be a more fitting place to stay during the Christmas season?) had speedy access to the city —  just 4 blocks from a T stop at Sullivan Station — but was far enough away to have a little breathing room, plus its own complimentary parking. Thanks to an extensive recent renovation the hotel looked polished and comfortable inside and included an on-site restaurant, “Draft,” for breakfast and dinner. The location in Somerville also offered an opportunity to explore the many wonderful dining, shopping, and cultural offerings in one of Boston’s fastest-growing neighborhoods.

In my room I found updated furnishings, a comfy bed, room to work, and a lovely view of the Zakim Bridge and city skyline in the distance. As a former resident of the city (and missing it quite a bit), I took every opportunity to enjoy it.

After a tasty dinner at the hotel, we made our way to Faneuil Hall Marketplace to admire the Christmas tree and watch a performance of Blink! Now in its second year, Blink! is a way to get a taste of the Boston Holiday Pops in a light-meets-sound extravaganza. Each hour 350,000 LED lights around the marketplace (including those on the 83-foot South Market tree) pulse and dance to the holiday music we all know and love. Get a hot chocolate and enjoy the show.

The next morning, one of the well-known orange and green Old Town Trolley Tours trolleys was waiting to whisk us around Boston. Our seasoned trolley driver (who went by Papa) offered up all the history, jokes (“I go for the groan!” he told us), and local knowledge the tours are known for, and it was especially nice to see so many of Boston’s famous spots decorated for the holidays.

And what visit to the city would be complete without trying a few new restaurants? For lunch we headed to cool and cozy Foundry on Elm in Somerville’s Davis Square, where I got a wild mushroom pizzetta made with truffle oil and parmesan. The dough was crisp and chewy (that perfect pizza combination), the mushrooms earthy, and the cheese a rich and salty delight.

After lunch we took advantage of the afternoon to explore some of Somerville’s new neighborhood ventures — including the shopping, dining, and entertainment projects underway at Assembly Row in the Assembly Square neighborhood and the outstanding new Brooklyn Boulders climbing/community facility in Union Square. Before heading over to see a performance of the famous Boston Holiday Pops, we visited Lucca in Boston’s beloved Italian North End for dinner. What came next was a terrific flurry of tastings — five courses in a row, all expertly paired. I used my phone to discreetly take sub-par (but hopefully still tasty-looking) photos of each non-meat course before digging in so you can see what we enjoyed. While everything was delicious, I have to say that my favorites might have been the start and end of the meal — the roasted beet salad with local burratta cheese was phenomenal, and what could be better to end a huge meal than cold, creamy spoonfuls of rich panna cotta? Especially when it had the added sweetness of apple cider marscapone!

Full of delicious food, it was time for some entertainment. The Holiday Pops is an annual tradition for many families in the Boston area, and it’s no surprise why. Each year during the month of December the Boston Pops dons its gay apparel and decks the halls (Symphony Hall, that is) with musical holiday cheer. The atmosphere is festive yet casual, and it’s hard to resist getting caught up in the holiday spirit when the traditional sing-a-long starts at the end of each performance…or when conductor Keith Lockhart kicks up his heels (clad in red socks) for a few seconds of can-can dancing during “The Twelve Days of Christmas.” In case you need an extra burst of merriment, each show also includes a visit from jolly old Santa Claus himself.

Other popular Boston holiday traditions include strolling Newbury Street for its window displays and gifts, Beacon Hill for its beautiful doorways and window boxes, and Boston Common for its tree, lights, and Frog Pond skating. Visitors also love taking in a show like the Nutcracker, Radio City Christmas Spectacular, or the annual Handel and Haydn performance of The Messiah. Do you head into Boston each Christmas season? Let us know your favorite things to do and see in the comments section!