Roundtrip Excursion: 44 hours in the hub of the universe

Hallie MacCormack and Jamie Stringfellow near the Westin Waterfront hotel in Boston's Seaport district. — Photo by Jamie Stringfellow

My daughter wanted one thing for her 17th birthday: to spend a weekend shopping off-Island for back-to-school clothes with the impressive amount of money she’d received from three sets of grandparents and two sets of parents. She drew up a list of roughly 44 stores, all of which she located at one giant mall situated somewhere in the suburban wilderness between Woods Hole and Boston. That provoked in me visions of a Lost Weekend (but involving way too much mall food instead of way too much whiskey) and made me so queasy I had to sit down.

“Hey,” I said to her. “Why don’t we go to Boston…?” Not as Google-maps-adept as she, but good enough, I’d soon plotted out a critical mass of her favorite stores in and around Boston proper. No mall food required, and we could walk from store to store in the glorious fall sunshine.

“Let’s go!” I said, and that Friday, off we went.

By Sunday afternoon, we’d both used up our budgets, but had just under 48 hours of fun, including room service (while she did her homework and I relaxed with the Sunday newspaper, overlooking Boston Harbor), sightseeing, great meals, and lots of happy miles under our feet. Here are a few of my favorite Boston things to do in fall that could please both adults and (miraculously) teens (and pretty much anyone else) in your family.

Just walk around

Often called “America’s Walking City,” the Hub is an ideal place to stroll. (Trivia: Boston was first called “The Hub of the Universe” by Oliver Wendell Holmes, who initially meant to refer to the State House as the hub of the solar system.) From our hotel on the waterfront, we walked up Summer Street until it turned to Winter at Downtown Crossing, where I regaled her with stories of my own back-to-school shopping trips with my mother at Filene’s, which is now being gutted to make room for something else. We walked through the Boston Common (America’s oldest public park) and continued to the Public Garden. We happened on a student playing Bach on a cello, while a bride and groom strode by in the opposite direction.

We wandered the HarborWalk; you can use the almost 47-mile route to connect the dots of the Harpoon Brewery, the Institute of Contemporary Art, Long Wharf, the North End, and beyond.

Then, of course, there’s the Freedom Trail and the Black Heritage Trail, which follow the paths to freedom that our ancestors trod, passing the Tea Party ship, Paul Revere’s House, and the 54th Regiment Memorial on the back side of Beacon Hill, dedicated to the African-American soldiers who fought for the Union in the Civil War. Good overviews of Boston Trails:;;; .

Or pedal

This has been on my list for a while: a foliage bike tour along Boston’s Emerald Necklace. When city officials — and more aptly, legendary landscape architect Frederick Law Olmsted — looked at swathe of green created by the Boston Common, the Public Garden, and the adjacent Commonwealth Avenue “mall,” they decided to keep going and create and link green spaces that, when viewed from above would look like, well, an Emerald Necklace. In the fall, Urban Adventours ( leads 15-mile bike rides through the foliage of the Boston Common and Public Garden, the Charles River Esplanade, the Arnold Arboretum, and the Rose Kennedy Greenway (Boston’s newest public park, sited on what was once the Southeast Expressway). They even supply the bikes!

Some really cool art

I think the Institute of Contemporary Art on the waterfront is itself a work of art. Framed views of Boston Harbor surprise you when you walk around a corner. We had lunch at Water, a Wolfgang Puck restaurant, outside in the sun, then wandered the galleries. I tried to restrain myself from asking my (painter) daughter, “What do you think this MEANS?” which would have elicitedd some major eye rolls, but other than that, it was relaxing and refreshing. The Museum of Fine Art, always a favorite destination for its impressive collection of Impressionist paintings and its musical instrument exhibit (check out the really tiny violin), has a show during October dedicated to “Hippie Chic.”

JFK Library

If we hadn’t run out of time, I would have gone to the John F. Kennedy Presidential Library and Museum in Dorchester in honor of the 50th anniversary of the President’s assassination. Just a short T-ride away from South Station, or an easy drive, the library is currently hosting exhibits about the Cuban Missile Crisis and Jacqueline Kennedy’s 1964 oral history interview, just unsealed two years ago. In addition to extensive artifacts relating to the President’s life and administration, the JFK Library also houses the world’s largest collection of Ernest Hemingway papers.


A little October baseball maybe? If seats at Fenway are hard to come by, there’s another classic October sport in town: the Head of the Charles Regatta, one of collegiate sports’ most prestigious events, held this year on October 19-20. More than 9,000 rowers from hundreds of colleges and clubs worldwide compete in races on the Charles River. Another 300,000 people crowd the banks under tents, tailgating, reuniting with old classmates, and just enjoying the (hopefully) spectacular October weather. Info:

If you’d rather stay inside, the Fall New England Home Show is November 1-3 at the Seaport World Trade Center.

Streetpianos? Yep, just what it sounds like — pianos placed outside in various spots around Boston — The Common, the Chinatown Gate, Faneuil Hall — so those inclined can sit down and play. But hurry: the pianos go away for the winter by month’s end. Info:


I think I discovered something about teenagers: Malls make them cranky and sarcastic. At least, in my own narrow scientific research, walking and moving around city sidewalks produces a far happier shopper. That and the close proximity to Victoria’s Secret, H&M, and Marshall’s, all within a few blocks of the Back Bay. With the shops at the Prudential Center and Copley Place nearby, no mall on the planet comes close. And it was fun to peer in the windows of Newbury Street — Chanel and longtime Boston Jeweler Shreve, Crump and Low, where we admired 20-carat diamonds. Faneuil Hall, Harvard Square, Downtown Crossing, and the one-of-a-kind boutiques in the North End are just short walks or T rides away.

Getting around

It’s pretty easy to go without your vehicle, so if you want to be car-free, the bus to South Station is the way to go. Save gas, parking fees, and the planet at the same time. Still, we all know, when the ferry prices drop, it’s cheaper to go with your car, and allows you a Trader Joe’s or Target run, which on its own can pay for your boat.

Parking can be tricky. Consider parking at Adams station on the Red Line for the weekend and taking the Red Line into town. Hotel parking can be pricey. The Boston Common Garage is about $10 cheaper per day than most hotels. In the end, if you park the car you can easily navigate Beantown on foot, or by pedicab, T, taxi, boat, or even bike. Check out this handy site to compare parking options:

Where to stay

Other than the shopping, my daughter said her favorite part of the weekend was our hotel (see Room Service, above…). We used and got a terrific deal at the Westin Waterfront, near the convention center. There are some B&Bs in Boston that are great deals, too. My friend Holly Nadler always stays at the Eliot & Pickett Houses on Beacon Hill ( for around $135 a night. For more in-town B&Bs, check

Where to eat

We love Trattoria Il Panino in the North End, and enjoyed an excellent meal and great atmosphere at the old-timey Mother Anna’s, also in the North End. Another favorite is the Paramount on Charles Street.