After All My Boston Winters, Here Are 5 Spots I Go To When It's Below Freezing

As someone who grew up in the hot and humid state of South Carolina, I was never built to withstand cold weather. I always appreciated SC's winters — yes, it does get cold there — but they were nothing compared to what I would experience living in Boston for the last three years. Boston's cold weather creeps in like a python stalking its prey. Stealthy, unsuspicious, until suddenly, it strikes. You realize the sun sets at 4:30 every day, and you can't feel your fingers after two minutes outside. It's only natural that once the Boston winter hits, seasonal depression starts to set in, leaving even the most staunch winter lovers (like myself) dreading leaving the house and bracing the cold.

I've learned that the best way to get out and face the actual windiest city in the U.S. (according to Climate and Weather) is to reward yourself with a place worth leaving the house for. Luckily, Boston has plenty of those, and this list contains my five favorites. While Boston may be on the list of U.S. cities to avoid for winter travel plans, I think you may want to consider it anyway. There's no better feeling than showing Boston's whipping winds that you're not afraid of them! Whether you're a tourist stopping in for a weekend or a resident who has to deal with the chill all winter, these places are a reminder that you can still have fun in the winter, even if your eyelashes are frozen together.

One of my favorite things to do on a frigid winter day is to cozy up with a good book at a café, which are conveniently in abundance in Boston. While this can end up being an overwhelming choice, there's one spot that book lovers shouldn't miss out on. Trident Booksellers and Café is located right at the mouth of Newbury Street and makes for the perfect bookish escape. It's easy to get lost in the shelves, wandering genres like romance, fantasy, memoir, literary fiction, and more. I find myself getting particularly lost in what I call the "catch-all section," full of board games, funky socks, and trendy book accessories. Pro tip: The best time to stop in is on a weekday. If you visit on the weekends, that's when you can expect to be squeezing through tourists to reach the shelves.

Once you find your book to read, head over to the café portion of the store. Be sure to bring an appetite, because this café doesn't just offer dinky pastries and finger foods. I'm talking giant pancakes, truck stop breakfast, and tasty sandwiches to munch on – not to mention the extensive list of hot drinks available to warm your hands back up from the windy walk to the store. Aromatic teas, creamy hot lattes, and (my favorite) a toasty hot chocolate. With the self-serve ordering system, you can even order a book straight to your table. The last time I visited, I took a gamble and went for the "Bookseller's Choice" for $10. One of the booksellers brought me The Girls by Emma Cline, a book I excitedly added to my ever-growing "to be read" pile.

Every tourist guide for Boston is going to tell you one thing: You want good food? Head down to the North End. Now, it's true; I've eaten at some truly divine Italian places in the North End, one of America's best little Italy neighborhoods. But the one thing that always makes it worth the trek is the post-dinner plans, better known as the Improv Asylum. According to the The Boston Globe, this comedy club is one of the best in Boston, and according to me, it is the best. There's nothing better than sharing an hour of laughs with a few hundred-some-odd strangers crammed into an intimate black-box theater while the performers do their best impression of a Victorian child using an iPhone for the first time.

As soon as you descend from the cold into the toasty basement theater and shuck off your coat, you'll know you've made it to the right place. Complete with a live piano player and an elaborate light system, performances at the Improv Asylum are a full sensory experience. You'll never see the same show twice, as each performance is heavily dependent on audience suggestions. For the holiday season, the Main Stage performances that run Thursdays through Saturday evenings have some holiday flair for their PG-13 Sleigh it Again! performances. However, outside of the holidays, the laughs are just as uproarious. If you're looking for something a bit more rated R, I recommend attending their naughty late-night performance, Raunch.

Of all of the wonderful museums Boston has to offer, the Isabella Stewart Gardner Museum is one of the best (and most criminally underrated) options available. Not only is the museum rich with history through the artworks and artifacts on display, but the museum itself is infused with its own personality and story that is just as fun to explore. Founded and curated in the 19th century by wealthy art collector Isabella Stewart Gardner, the museum boasts an impressive collection of Asian and European art. While Gardner was alive, the museum served as her home, office space, and life's passion.

Isabella's personal touches and influence are alive through the way she organized the space, the art she chose to keep, and most obviously through the extravagant courtyard in the center of the museum that overflows with greenery and stone statues. Entering this lush courtyard in the wintertime, under the full-ceiling skylight, feels like stepping into summer — a rare occurrence in the dead of Boston winter. When you wander the museum, keep your eyes peeled for empty frames. This is where the paintings stolen in the largest property heist in U.S. history used to be kept before they were swiped by thieves in 1990. The heist has yet to be resolved to this day, with the museum still holding out hope that the lost art will one day be returned.

In addition to Isabella Stewart Gardner's Personal collection, the museum also offers several seasonal exhibits that change throughout the year. Adult admission is $22, which I recommend buying ahead of time, as the museum tends to sell out quickly.

Located in another Boston tourist hot spot, the Frog Pond Skating Rink is one of the few attractions worth staying outside for. After spending the afternoon wandering America's oldest public park, the snow-covered Boston Common, lace up your skates for some time out on the ice. If you're over 58 inches tall, admission is $12 (not including ice skate rental). However, little ones get in for free. My favorite time to visit is after the sun sets, so I can see the park lit up by both the holiday displays and city lights. If you're in town on New Year's Eve, be sure to stop in for the Frog Pond Skating Spectacular; two free performances to ring in the New Year.

Whether you brought along a little one who needs help skating, or you simply need some help, you can splurge an extra $20 for the adorable Bobby the Skating Seal aid. There's no shame in bringing this little guy out on the ice with you. After some time spent elegantly gliding across the ice (or falling on your butt), you may work up an appetite. This is the perfect excuse to grab a bite at the Frog Pond Café. To warm up and get into the holiday spirit, I recommend a toasty hot chocolate or warm apple cider to take the chill off your frozen fingers. Just be sure you're done skating for the day when you step off the ice, as you'll have to pay admission again if you want to reenter the rink.

My final (and classiest) recommendation for Boston's best cold-weather activities is none other than an evening out at Symphony Hall. This legendary concert hall is home to the Boston Symphony Orchestra and Boston Pops, as distinguished by the glowing red letters lighting Huntington Avenue. During the holiday season, the Boston Pops is going to be playing your typical holiday tunes approachable for any audience. December shows include Kids Holiday Matinees, Elf: In Concert, and A Charlie Brown Christmas: Live at the Symphony. Year-round, the Boston Pops transcend musical genres, playing tunes from classical to Broadway to jazz.

Once the holiday season passes, the majority of winter showings will be performed by the BSO, the renowned Boston Symphony Orchestra. From string quartets to Tchaikovsky piano concertos, every performance will have your eyes closed and head swaying. It's the best way to warm up the creative side of your soul on a chilly Boston evening. 

Not only will the music that echoes through Symphony Hall amaze you, but the stunning interior is a work of art in itself. When you enter the hall, be sure to look up to catch a glimpse of the ornate design of the hall. I could stare at the marble statues adorning the perimeter of the theater forever. A night out to Symphony Hall is the perfect conclusion to a romantic winter date night, or a holiday treat for the little ones. There's just something about snowflakes and symphonies that pairs so well.