Boston in a Weekendfeatured

When our Europe trip took up most of Stephanie’s days off for the year and we had to push our annual October family getaway to Christmas, I started looking for destinations for a short weekend trip.

Weekend trips are tricky. If you fly out Friday night and fly home Sunday night, you have a day and a half to explore. It’s not for everyone. Some people won’t see the worth in having a couple of days to take in a new city. For me, though, any chance to experience a new place, however short the trip, is always worth it. I find a new energy when I’m traveling. And short trips? They force us to take advantage of our time to wander around. There’s literally no time to waste.

But as much as I love short trips, I’m firmly against paying long trip prices for short getaways. So when we had exactly one weekend to go somewhere, I turned to Google Flights to tell me where we were going. I can find a cheap hotel anywhere, and cheap rental cars are even easier to come by. But cheap airfare? That’s always the hurdle.

The cheapest flights out of Chicago for Halloween weekend were to Los Angeles, New York, Boston and Dallas. We couldn’t come to a consensus on what we’d do with a day and a half in Los Angeles (Stephanie would want to go to Disneyland and I’d want to wander around Beverly Hills), the cost of going to New York would almost double with meals and theater tickets and we didn’t know what we’d really do in Dallas, but Boston was an interesting option. Everyone I know who has been to Boston comes home telling me stories about how much they loved Boston. Big city with a ton of history? Sounds like my kind of place. But could we get in all of the big stuff in a 48 hour trip?

We did. And it was awesome.

So how do you see the best of Boston in one weekend? This is what we did:

Visit the Oldest Baseball Stadium in the US

As a long-suffering Cubs fan, there’s no team I feel a deeper kinship to than the Boston Red Sox. After all, not only did they suffer through the second longest World Series drought (and come out of it with multiple World Series wins, thanks in large part to front office staff we poached from them!), but they play in the only stadium older than my beloved Wrigley Field.

We went early in the morning and there was literally no one else around, giving us a unique opportunity to wander around and appreciate Fenway without interruption (and give me an opportunity to randomly yell out NOMAR GARCIAPARRA a la this SNL sketch without getting weird looks). They offer hour long tours inside the park (unfortunately, the Fenway in 15 Minutes tour is only offered during the summer!), but with such limited time to explore the city, we opted to just admire it from the outside.

Check In on the Local Coffee Scene

One of the tenets I try my best to live by is to not dine any place I have at home when I travel, even when I’m just looking for a cup of coffee. I was approaching hangry status by the time we left Fenway, so when popping into the closest Starbucks just wouldn’t do it, I typed coffee into Google Maps and we headed towards the one with the most unique name.

We ended up at Flour Bakery in Back Bay, grabbing some pastries to eat at the counter (there were no tables in a decently sized space — always good reinforcement that you’ve made a good choice!) and some latte’s to take with us while we strolled.

Go to the Mall (…No, Not That One)

It wasn’t on our to-do list, but when we walked past the Commonwealth Avenue Mall on our way to breakfast and saw the canopy of crisp, colorful leaves shading the sidewalks of the park, we knew we couldn’t leave without a stroll.

This mall dates back to the mid-1800s and was like a haven of peace nestled into the bustling city. Tall trees sprouting leafs in vibrant fall shades flanked the walkway, providing the perfect shaded spot to enjoy those lattes.

Tour a Local Brewery

I have to admit it — I don’t like beer. Stephanie’s been on a mission to find a beer that I can get more than three sips into without giving major scrunch face since college. My friends (craft beer aficionados, themselves) have given up on trying to help me acquire an appreciation for it (and constantly remind me that cider ≠ beer. And Radlers don’t count, either. Or so they say.). I got to go to Fenway in the morning, so Stephanie got to do a brewery tour in the afternoon. Compromise.

Harpoon Brewery was a name that kept coming up when she was looking up local craft brews, an employee-owned brewery that offered tours and crafted both beers and ciders. Win-win for both of us. The brewery is right on the water in a cool, industrial space. There wasn’t much of a wait for the tour when we got there ($5, including unlimited tastings in the tasting room), but the beer hall was hopping and the line wound around the building when we left. Timing is everything when you don’t have much time to spare.

The tour lasted around an hour, and took us into the belly of the brewery, right where all the action took place (and by action, I mean where the beer is born. Lots of it, too — Harpoon is one of the largest craft breweries in the US!).

I sampled a couple of beers but all samples resulted in scrunch face. Their cider was primo, though. And Stephanie (who can actually get past three sips of beer) really enjoyed many of their brews. After our tour, we ended up in the Beer Hall, with a cider for me, an IPA for Stephanie and some jumbo soft pretzels.

Harpoon doesn’t have a restaurant. The only food they serve is soft pretzels, but these aren’t your run of the mill concession stand pretzels. These pretzels are boiled in Harpoon’s IPA, studded with malted barley and flanked by two dipping sauces (they offer eight options!). Solid A+ in my book.

So I may not enjoy beer. That didn’t change. But super interesting tour + good cider + carbs with multiple dipping sauce options? Definitely worth it.

Explore the Freedom Trail

The redcoats are coming! The redcoats are coming! No, seriously, I said this enthusiastically and out loud. Because history is awesome and getting to walk through the heartland of the American Revolution is awesome.

The Freedom Trail is a two and a half mile path that has stops at 16 historical sites. Two and a half miles doesn’t sound like a lot and walking the entire path and crossing all the sites seemed doable in thought, but when you get on the trail and you’re walking uphill, downhill and spending time exploring the sites, the idea of doing it all becomes far more daunting.

So we didn’t do it all. We couldn’t have even if we wanted to. We saw what we could, we took our time to explore whatever seemed interesting and we were perfectly satisfied with that approach. We walked through the Old City Hall, we explored the site of the first public school, we left a penny on Paul Revere’s headstone (because a penny saved is a penny earned, you know) and we explored two burial grounds.

Touring Europe last Spring was such a profound experience for someone who loves history the way I do, and it’s easy to forget about the kinds of history in our own backyards (or, you know, a short hour and a half jump to the East Coast). The sites along the Freedom Trail represent such significance in American history and best of all, it’s not a trek from city center — the heart of Boston was built around these sites. It’s really something special.

Walk through Faneuil Hall and Shop at Quincy Market

When we started trekking around the Freedom Trail, Stephanie had her eyes open for Faneuil Hall and Quincy Market, and when we found ourselves approaching, I initially didn’t see the big deal. Faneuil Hall was just a building and Quincy Market had two big banners for UNIQLO hanging from it, hardly historic, right?

Wrong.

Faneuil Hall has been a central marketplace serving the Boston area for over 250 years. In the Revolution era, it also served as a gathering space for people like Sam Adams (yeah, the beer guy) to give speeches and rally support against Great Britain. And Quincy Market? National Historic Landmark built in the mid-1800s and constructed with zero debt.

It’s interesting to see how the modern brick-and-mortar shopping experience has merged within two historical landmarks, and it reminded me a lot of Navy Pier at home.

There are dozens of dining options between Faneuil Hall and Quincy Market and the walk through marketplace, the food court, the carts outsides, the bars and the traditional sit down restaurants within them. We weren’t quite hungry for a full meal, though, so we tracked the Cookie Monstah food truck down the street and grabbed a snack there.

[Valet]ed the Car in the Harvard Yard

Our flight home on Sunday wasn’t until the late evening, which gave us almost a full day to explore more of this gorgeous city. Having crossed Fenway, the Freedom Trail and a brewery tour off our lists, we decided to drive out to Cambridge to visit Harvard.

We probably should have taken the Red Line in (the subway stop is literally right outside the gates), but we had luggage in the trunk and a flight to catch later on. Finding parking was nearly impossible — aside from the university, Cambridge has a ton going on, including some great shopping and a lively brunch scene. It’s the perfect place to spend a Sunday morning.

So we valeted the car in a nearby lot, walked around the quad and grabbed a cup of coffee in a nearby cupcake shop. And we bought shirts in the Harvard bookstore. You know. To commemorate the time we got into Harvard (geographically, anyways).

Brunch Like Bosses

One of the best parts of exploring new places is exploring the local dining scene. My favorite meal to do this? Brunch. Brunch is the best meal of the day, if you ask me. And Boston? Boston knows how to brunch.

Boston loves brunch so much that we couldn’t get into the first *three* brunch places on our list in Cambridge. Undeterred, we drove out to nearby Newton, to see if we could get in at Cook., a restaurant that used fresh, locally sourced ingredients and seemed to appear on many of the top brunch lists. Even though the restaurant wasn’t full, without a reservation, they could only offer us bar seating. And though the service was decent (at best), the brunch fare was top notch. Veggie Benedict with a smoked tomato hollandaise? Yes, please.

Climb the Bunker Hill Monument (or Try To)

I do dumb stuff sometimes. You know. Like that time (or two) when I climbed on top of a cannon that was perched over a cliff in St. Kitts to take a picture for my Facebook profile. My Mom likes to bring that one up every few months.

We had a couple of hours before we needed to head to the airport after brunch, so we decided to visit the Bunker Hill Monument, which sits across the river, on the far end of the Freedom Trail.

So we go into the lodge and I’m thinking how cool it would be if people could climb the actual monument. And apparently you can. You can climb all 294 steps to the very top. And I like a good challenge. 294 steps doesn’t sound like a lot, does it? We climbed all kinds of shit in Europe. Stephanie looked at me, rolled her eyes and told me she’d be waiting for me at the bottom.

Do you know that 294 steps is 22 stories? You probably do. But I definitely didn’t. Which is how I got about 180 steps up (they even number them so you can track how high you’re getting) before I realized that if I climbed any higher, I wasn’t going to be able to get back down. And I kind of stood there for awhile, trying to contemplate if the views from the top and the satisfaction I’d get in getting there would be worth the extra effort of dragging myself up another ten stories. When I realized I was hopping on an airplane in a couple of hours, where I’d be sitting for two hours on an airplane back to Chicago after attempting to climb a 22 story monument, I realized I was pretty fucked and my muscles were going to plot their revenge on me the entire flight back, and I marched myself back down.

Spoiler alert: definitely could not take any kind of steps up or down for a solid three or four days after we got home. That made getting on and off the CTA buses super fun. Moral of the story? Go see the Bunker Hill Monument. Do not attempt to climb it right before your flight.

The One Thing We Didn’t Do

After I climbed down (and was greeted by my sister, who told me she knew I didn’t make it to the top when she didn’t see an Instagram post proclaiming my own victory), I popped a couple of Advil and we hopped in the car to make one last quick stop: the North End for some cannoli.

Boston’s North End is home to their Little Italy, a community of small Italian shops and restaurants. Two in particular, Mike’s Pastry and Modern Pastry Shop, top all of the must-visit lists we’d found. We’d driven through the North End the night before, hoping to find a place to grab dinner but not finding any parking, so we came back with a plan: Stephanie would circle while I’d hop out to get the cannoli’s.

Did you know that these small pastry shops are cash only? Me, neither. No cannoli for us. Next time, Boston.

Have you ever been to Boston? What’s on your must-see list?