Two films made Boston feel like a character on screen, and both starred Matt Damon. Good Will Hunting, from 1997, written by Damon and Ben Affleck, turned a plain bench in the Public Garden into a place of pilgrimage. The Departed, from 2006, Martin Scorsese's remake of the Hong Kong film Infernal Affairs, told a story of two moles, a young cop hidden inside a gang and a gangster's man hidden inside the police. Here's the twist this walk keeps coming back to: neither film was made mostly in Boston. Much of Good Will Hunting was shot in Toronto, and more of The Departed was filmed in New York than here, on real streets and on sets in a Brooklyn armory. So at every stop you'll hear what was filmed here, what was faked somewhere else, and what stands here now. You'll start with a TV bonus at the Cheers pub, sit near the Good Will Hunting bench, then follow The Departed from a Charles Street storefront across the Common, past the gold dome, through Chinatown and South Station to the Fort Point rooftop where its endgame plays out. This is an unofficial fan walk, not made with or endorsed by the studios, networks or filmmakers. It's one of our self-guided walking tours, about 3.7 kilometers from 84 Beacon Street to Farnsworth Street in Fort Point.

Before you set off

Allow about 55 minutes of walking, and an hour and a half or more with the stops. The route climbs a short hill on the Common and up toward the State House, and is otherwise flat city sidewalk. To reach the start, the Arlington station on the Green Line and the Charles/MGH station on the Red Line are each about 500 meters away. At the end, South Station is about 550 meters back the way you came. Daylight is best. Cheers is a working pub and the other stops are shops, stations, a church corner and offices, so look from the sidewalk and keep doorways clear. Expect spoilers for both films, and know that The Departed is violent, though nothing on this walk dwells on it.

Cheers (Bull & Finch)

You're on Beacon Street, across from the Public Garden, outside number 84. Look for the steps leading down from the sidewalk and the sign hanging above them. This is Cheers Beacon Hill, a working pub, and the warm-up act for this walk.

It opened in 1969 as the Bull and Finch, founded by Thomas A. Kershaw. When the creators of a new TV sitcom went looking for a Boston bar, they found this one through an ad in the Yellow Pages. The producers paid one dollar to use the outside of the building for establishing shots. And that's all the show ever used. Cheers was filmed on a set in Hollywood. The basement bar down those steps doesn't look like the bar you saw on TV.

But fans came anyway. In 2002, under a licensing deal with CBS, the pub was renamed Cheers Beacon Hill. A gift shop and a replica of the TV bar were added on the ground floor.

Keep this stop in mind, because it sets the pattern for everything that follows. A real Boston front, and a fake Boston inside. Both of our films worked the same way. Hollywood came to Boston for its look, then built much of the rest somewhere else.

Our first film is just across the street. It's the story of a young man named Will and the therapist who finally reaches him, and one of its best-loved scenes happens on a bench by the water.

Cross Beacon Street into the Public Garden and walk to the footbridge over the lagoon. From the western end of the bridge, follow the lakeside path north. The bench is the third one along. About four minutes.

Good Will Hunting Bench

You're at a plain wooden bench on the path beside the lagoon in the Public Garden. There's no plaque and no official marker. If it's free, sit down and look out over the water.

In Good Will Hunting, the therapist Sean Maguire, played by Robin Williams, brings Will, played by Matt Damon, to this spot for a heart-to-heart talk. Two men on a bench, looking out over the water, and one of them finally getting through to the other.

The scene is one of the film's real Boston moments. A lot of the rest was not. Much of Good Will Hunting was made in Toronto, including interiors shot at the University of Toronto. Even the famous Harvard bar scene was filmed inside a bar in Toronto.

The film was honored at the 70th Academy Awards, on the 23rd of March, 1998. Robin Williams won Best Supporting Actor, and Damon and Affleck won the Oscar for original screenplay.

Then this bench took on a new meaning. After Robin Williams's death in August 2014, people came here with flowers and notes, and wrote lines from his films in chalk on the pavement. This ordinary bench became a memorial.

You may hear there's a statue here. There isn't. In 2024, Matt Damon backed an artist's proposal for a bronze statue of Williams sitting on the bench, but it was only a proposal.

Now to the second film, and a much darker Boston. Continue along the path to the garden's corner at Beacon and Charles Streets. Cross Beacon Street and walk a short way up Charles Street to number 17. About four minutes.

Charles Street Cleaners

A gas-lit Beacon Hill side street, Boston

You're on Charles Street, outside number 17. Today it's Charles Street Cleaners, a dry cleaner. Please look from the sidewalk and leave the door clear for customers.

In The Departed, this storefront became a bar. The crew dressed it as the Charles Street Brasserie, the hangout of Frank Costello, the crime boss at the center of the film.

Step inside, though, and you'd be in New York. The bar's interior scenes were shot at Raoul's, a restaurant in SoHo, Manhattan. So the film's gangster bar is a Boston face on a New York room. The story goes that Scorsese turned down the real bars on this street as too nice for South Boston gangsters.

A word about Costello himself. People often compare him to Boston's real gangster Whitey Bulger. Paul Sherman, who wrote about the film's Boston locations, says the script adds touches that echo Bulger, but most of the character comes from Infernal Affairs, the Hong Kong film The Departed remakes. Treat him as an echo of Boston history, not a portrait of it.

Here's the setup of the story. Costello has his own man inside the Massachusetts State Police: Colin Sullivan. And the police have their own man inside Costello's gang: Billy Costigan. Two moles, each hunting the other. And one early look at the police side of the story comes on a sports field.

Walk back down Charles Street to Beacon Street and cross Charles Street into Boston Common. Climb the hill to the tall Soldiers and Sailors Monument. About five minutes.