The five best things to do in Boston's Seaport District

The director of Boston's renowned Institute of Contemporary Art shares her picks for the best ways to explore Boston's fastest-growing neighbourhood.

Boston, the birthplace of American independence, is often described in a historical light. But centuries after Paul Revere's midnight ride and the Boston Tea Party, "Beantown" has evolved into a dynamic destination that's as contemporary and cosmopolitan as the nation it inspired – and nowhere is this more evident than in its Seaport District.

Once dismissed as an urban wasteland, decades of redevelopment have seen this stretch of the South Boston waterfront reborn with sleek new restaurants and bars, hotels with rooftop pools and modern parks. One of the biggest drivers in the district's transformation was the relocation of the world-class Institute of Contemporary Art (ICA) to the District in 2006.

"When we moved there, we were surrounded for as far as the eye could see almost entirely by above-ground rubbly parking lots. When we opened, there was just widespread amazement," said Jill Medvedow, who has been the ICA's director since 1998. "My involvement and understanding and experience with the Seaport really has been as a kind of central person, player and observer of wholesale transformation since then."

These days, perhaps no one knows the Seaport better than Medvedow. Here are her recommendations of what to do in the area.

1. Institute of Contemporary Art, Boston (The Grandstand)

Fittingly, Medvedow's favourite spot in the Seaport is the ICA, but the place she loves most isn't inside a gallery. "One of the things that is so wonderful about our museum is our Grandstand, the seating that faces Boston Harbor," she said. "It is always open, always free to the public. You can see East Boston, the airport, downtown, boats, yachts, liners and tankers, kayakers and walkers. It is fantastic. You really have a sense and a very unusual perspective on Boston. It is just spectacular."

The ICA cuts a dramatic figure in the Seaport and was designed by award-winning architects Diller Scofidio + Renfro. The unusual 65,000 sq-ft building is cantilevered and features transparent glass, translucent glass and opaque metal, making the most of its harbour views. Its open-air Grandstand area attracts both locals on their lunch breaks and tourists taking selfies on the steps, and it's also a regular backdrop for celebratory opening events and dance parties. "Sunset [here] is extraordinary," said Medvedow. "In the summer months, we frequently see rainbows. But honestly, the view is always an uplifting combination of light, shadow, salty air and sky – unique in all of Boston." 

Website: https://www.icaboston.org/

Address: 25 Harbor Shore Drive

Telephone: +1 617-478-3100

Instagram: @icaboston

2. Tatte Bakery & Café

With Tatte's 22 locations in Massachusetts and 10 in the Washington, DC area, founder Tzurit Or may seem like she has a background as a restauranteur, but the Israel-born pastry chef is a former film producer who left Tel Aviv to start a new life in the US. The self-taught baker launched her budding empire from her home, selling baked goods at a weekly farmers' market in Boston's Copley Square in 2007, opening her first brick-and-mortar cafe in 2008. In less than two decades, Or catapulted from her home kitchen to more than 30 locations, with no signs of slowing down any time soon.

"My second office, I would say, is Tatte," said Medvedow. "You will frequently find me getting Tatte's halloumi salad, which is outstanding." Or mixes the salad with locally sourced baby lettuces, seared halloumi cheese, roasted carrots with sesame and raisins, radish, apples and crunchy almonds in a tahini vinaigrette. Tatte's Seaport location (a block away from the ICA), has a European vibe, with white subway tiles on the walls and freshly baked goods on display behind glass on the counter. Besides Medvedow's salad, the menu features items like a traditional North African shakshuka (poached eggs in a simmering tomato sauce with spices), a variety of tartines, vegetable bowls and sandwiches.

Website: https://tattebakery.com

Address: 200 Pier 4 Boulevard

Phone number: +1 617-765-7600

Instagram: @tattebakery

3. Porter Square Books: Boston Edition

Located in the GrubStreet Center for Creative Writing, Porter Square Books: Boston Edition is the sister of the original and popular Cambridge store, known for its "fiercely independent" tagline. The flexible space features bookshelves and displays mounted on wheels, so it can be reconfigured for different events when needed. There are innovative and inclusive programmes and events on offer, from silent book reading parties to a writers-in-residence programme to encourage customers to donate books to prisons. Having a second home within GrubStreet made perfect sense, and as Medvedow said, it was a welcome addition to the neighbourhood. "It was so needed," she asserted. "They brought fiction to the Seaport. The ICA Store's selection of art books can't be beat, [and] I need a well-selected choice of contemporary fiction."

Inside the Seaport shop, there's a cafe, plenty of spots to sit and browse, and a small events stage for book signings and lectures. Don't miss the whimsical display of brown-packaged books with hidden titles called "Blind Dates", with labels inviting you to take a chance on a mystery, romance, news or general fiction book. Slipping into the shop, where customers may be sipping on a latte or flipping through books in a corner, offers a quiet respite from the busy Seaport streets.

Website: https://www.portersquarebooks.com/

Address: 50 Liberty Drive

Phone number: +1 617-675-9760

Instagram: @porter_square_books

4. Cardullo's Gourmet Shoppe

Another Cambridge staple, Cardullo's, made its way to the Seaport in 2018, much to local chocolate lovers' delights – such as Medvedow. Opened in 1950 and still family-owned and operated, the gourmet grocery store is beloved for its sweets but also known for its generously-sized and freshly-made sandwiches. There is a small deli counter tucked on one side where you can pick up breakfast or lunch to go.

As you enter the store's narrow opening, there's no avoiding temptation in the form of a wall of confections to your left, stocked with Belgian truffles and chocolates, German marzipan creations, French chocolate bars, Canadian marshmallows, Swedish fish candy (really made in Sweden), and more local specialties, such as Cape Cod sea salt caramels and chocolate bars made in Vermont. Head deeper into the shop and it opens up to floor-to-ceiling shelves offering a huge variety of wines, liquors, oils, vinegars, cheeses, cold cuts, condiments and even a selection of caviar and tinned fish. But for Medvedow, it's all about the chocolate. She said, "The last time I was there, I tried Icelandic dark chocolate with sea salt. Delicious, and I love Iceland!" 

Website: https://www.cardullos.com/

Address: 99 Seaport Boulevard

Telephone: +1 617-326-8655

Instagram: @cardullosshoppe

5. John Joseph Moakley Federal Courthouse

"The facade of the Moakley Federal Courthouse has a series of quotes on democracy and government," said Medvedow. "There are quotes from [social reformer] Frederick Douglass, [US President] John F Kennedy, [American abolitionist] Sarah Grimké and others, and every time I walk back and forth – and this is many, many times a week – they are inspiring. They ask us to be our best selves as citizens and participants and upholders of democracy. It's really a wonderful part of the Seaport that I wish everyone would read."

The courthouse was completed in 1998 and serves as the headquarters for the US District Court for Massachusetts. The courthouse's 40 inscriptions can be found both inside and outside the building and are carved into large grey granite tablets. On Courthouse Way, outside, you'll find tablets containing parts of the Declaration of Independence, the preamble to the United States Constitution, plus parts of important amendments, showing how the US is always striving to be a more perfect union. The indoor inscriptions and more artwork are located throughout the courthouse in the main lobby, the grand rotunda, the Atrium, upper galleries on the third, fifth, and seventh floors, and the lower galleries at the Harbor entrance – all of which are open to the public and free to visit. 

Website: https://www.gsa.gov/about-us/regions/region-1new-england/buildings-and-facilities/massachusetts/john-joseph-moakley-us-courthouse

Address: 1 Courthouse Way

Phone number: +1 617-748-9152

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