WORDS + PHOTOS BY MARC HURWITZ
A couple of years back, I compiled a list of welcome-back walks that took students and others to places in and around Boston proper that aren’t your typical jam-packed touristy spots. Those hikes only scratched the surface, so here’s another lineup, and this time there are options for food and drink along the way—plus we included other communities in the region as well.
Harborwalk, Boston’s Seaport District
The stretch of Boston waterfront from Fan Pier and Fort Point Channel eastward to the marine industrial park can feel like a pretty soulless place, especially if you drive through it without getting out of the car, but behind the endless residential towers and office buildings is one of the most scenic walking paths in the entire region. Starting from the area around the Barking Crab and the Moakley Courthouse, you can stroll along the water uninterrupted for a pretty good stretch, with many sites being found along the way, including docks, a pavilion that you can climb (incredible views from the top), little strips of parkland, and one pier after another that heads out into the ocean. If you get hungry and don’t want to spend a fortune, J. Pace & Son and its sublime Italian subs await you near the eastern edge of the walkway.
[Directions: From downtown Boston, take Seaport Boulevard over Fort Point Channel, then take a left on the east side of the channel.]
Huron Village/Observatory Hill, Cambridge
The city of Cambridge has lots of bustling neighborhoods, but this section just west of Harvard Square definitely isn’t one of them. Buried inside the heart of Cambridge is basically a charming village with a small-town feel complete with small independent shops and restaurants, gorgeous old homes, and tree-shaded roads that make their way up and down the little hills here. Huron Village itself lies along Huron Avenue a short distance south of Concord Avenue, while Observatory Hill is where the two streets meet—and near where they meet is a fantastic little pizzeria called Armando’s where you can grab a slice and make your way to nearby Fresh Pond if the weather is nice.
[Directions: Red Line to Harvard, then walk up Garden Street to Huron Avenue and take a left.]
Savin Hill Area, Dorchester
Dorchester is a huge neighborhood of Boston that has a lot of interesting sites, and it also has its share of green (and blue) space, with some of the nicest options for quiet walks and water views being in this neighborhood just off the Southeast Expressway. A great walk that includes a bit of everything starts at the JFK/UMass T stop where you can pick up a section of the Harborwalk that winds around Columbia/Harbor Point over to UMass Boston, then leaving the water, you cross Morrissey Boulevard to Old Colony Terrace and Savin Hill Avenue where you’re suddenly in a quiet neighborhood of huge old homes. Savin Hill Park sits in the middle of this tiny neighborhood, high above the houses and with ocean views that look like something you might see in Maine. If you’re here around breakfast or lunchtime, McKenna’s Cafe on Savin Hill Avenue will give you a feel of what a true local hangout is like.
[Directions: Red Line to JFK/UMass, then right on Columbia Road/Day Boulevard and take a right on the Harborwalk just before Carson Beach.]
Brookline Staircases
One of the most fascinating (and strenuous) walking options in the Boston area, the public staircases and paths of Brookline are very little-known but a great way to catch some views and maybe train for whatever it is you train for. Most of the staircases and steep pathways are situated around two hills that more or less face each other above Washington Square—Corey Hill and Aspinwall Hill—and and some are extremely short while others (like the thigh-burning Summit Path, which leads from Beacon Street to the top of Corey Hill) are long enough to force you to take some breaks. Approximately 15 of these staircases and paths can be found on these two hills, which should be more than enough—and if you build up an appetite from doing them, there are countless dining and drinking spots down below, including the Publick House on Beacon Street, which is a must if you love beer.
[Directions: Green Line to Washington Square.]
Southwest Corridor Park, Back Bay/South End/Roxbury/Jamaica Plain
A long time ago, there was a plan to build a highway from Boston southwestward directly to where Routes 95 and 128 meet in Canton. This plan was ultimately killed, but the section where the highway was supposed to cut through remained wide open, and eventually this linear park was created, allowing for a rather unique oasis of peace and quiet through some of the busiest parts of the city. The walkway begins off Dartmouth Street next to Copley Place and continues all the way down to JP, with some of the most interesting parts skirting the northern part of the South End where you’ll see very British-feeling roads right off the path. And if you’re looking for food, the South End has too many places to mention, though for a great experience, Anchovies is close by on Columbus Avenue and is a Boston classic complete with old-school Italian-American fare.
[Directions: Take a right off Dartmouth Street just after Copley Place in the Back Bay.]
Tufts University, Medford/Somerville
The staircases of Brookline may give you a better workout, but if you’re looking to burn some calories while enjoying some surprisingly great views from a college campus, the Medford and Somerville campus of Tufts is definitely worth your while. Unlike some of the others here, there’s no set path to take, but meandering along Professors Row, Packard Avenue, and all the walkways around them will keep you busy for awhile, and one poorly kept secret—at least among Tufts students—is the view from the roof of the Tisch Library, which puts some of the views from the hilltops of the nearby Middlesex Fells to shame. The neighborhoods around Tufts have lots of great dining options, one of the best of which is Tasty on the Hill on Boston Avenue in Medford, which features Portuguese food, including francesinhas, or sandwiches that include everything but the kitchen sink.
[Directions: Red Line to Davis, then walk north on College Avenue to the campus.]
Pope John Paul II Park, Squantum Point Park, Marina Bay, Dorchester/Quincy
Part one of this list included the Neponset River Greenway, which heads west from Pope John Paul II Park, and while it is a beautiful walkway with lots to see, going the opposite direction will get you to some great ocean views. Walking over the Neponset River Bridge by the northern part of the park will get you from Dorchester to Quincy where you head north along Commander Shea Boulevard and look for a path to the left just before the Boston Scientific building. This trail goes along the east side of the Neponset River and eventually brings you to Squantum Point Park with its views of the Boston Harbor Islands, the iconic Dorchester gas tank, and the Boston skyline. From here, you can head east into Marina Bay, which is a resort-style area with a boardwalk and a number of restaurants and bars, including Siros, a slightly upscale but reasonably priced Italian restaurant with views of the water.
[Directions: Red Line to Fields Corner, then bus #202 to Hilltop Street at Hallet Street just west of Pope John Paul II Park.]
Fort Point Channel, Boston
Another part of the Harborwalk, one that can be combined with the Seaport District section above, this walk includes some fascinating areas that have yet to be discovered for some reason. A good starting point is from the west side of the channel just east of South Station, where you can walk north along the water up to Seaport Boulevard, take the bridge over the channel, and work your way back southward along the east side of the channel. Some jaw-dropping views of the Boston skyline can be seen here, especially around the Children’s Museum, and once you cross Summer Street, you end up in another world, entering an old industrial area of Fort Point with endless views of the skyline while possibly having the entire path to yourself. Once you get to the end of the channel just before Broadway in South Boston, you can retrace your steps and see the walkway from a different angle, or continue into Southie where you have many dining options, including the decades-old Mul’s Diner, an institution that manages to hang on in the middle of massive new development along Broadway and beyond.
[Directions: From South Station, take a right on Summer Street and then a left just before the bridge.]
Agassiz Neighborhood, Cambridge
Much like Huron Village and Observatory Hill (see above), the Agassiz section of Cambridge is within walking distance of the always-busy Harvard Square but feels like it is a million miles away. And while it doesn’t have a charming commercial strip like Huron Village does, it does have the feel of being its own little community with its winding streets, stunning old homes, and huge old trees. This is another one of those places where you just want to pick a direction and walk, perhaps heading east off Mass Ave between Porter Square and Harvard Square and wandering around aimlessly while trying to stay between Mass Ave, Cambridge Street, and Kirkland Street, which mostly form the border of Agassiz. By the way, this neighborhood is where Julia Child lived, and if that makes you hungry (and how could it not?), heading back to Mass Ave to Cambridge Common might not get you a gourmet French meal, but it will get you some outstanding chicken tenders and a beer list that always impresses.
[Directions: Red Line to Harvard, then walk north on Mass. Ave. for a few blocks before taking a right on any of the side streets.]
Dorchester Heights, South Boston
A short but sweet walk, and one that can include that ever-present Harborwalk, Dorchester Heights may not be a huge area, but it is one where you can spend a lot of time if you want to get away from it all (and high above it all) while still being near the heart of Boston. From the JFK/UMass T stop, take the same route that you would to Savin Hill above, but instead of going right on the Harborwalk toward UMass at Carson Beach, take a left instead and follow the beach on your right for a bit until you get to the traffic light where Day Boulevard meets up with Columbia Road. Here you’ll notice one of those weird “frontage” roads that only Boston seems to have, and yes, this narrow residential street is considered Columbia Road as well for some reason. Take a left on the frontage road, then a right on Covington Street, and try not to swear, as you’ll see a steep road that eventually gets too steep to actually be a road and turns into a staircase. At the top of the staircase is Dorchester Heights, a small park with views of Boston and the ocean that will probably make your knees weak. Once you’re done soaking up the views, head back down the staircase and head right into the Seapoint Bar and Grill, a local hangout with lots of characters and some of the best pizza you’ll find anywhere in the city.
[Directions: Red Line to JFK/UMass, then right on Columbia Road/Day Boulevard, then follow the Harborwalk north along Carson Beach.]
Marc is the founder of @hiddenboston, a textbook editor, a hike leader for @AppMtnClub, and a food and travel writer and commenter for DigBoston, NBC/NECN, WBZ, WMFO and indie617.
