Hikes that will help you get to know Boston better

Early fall is a time when Boston always sees a lot of new faces, and if you’re new to the city, it can seem a little overwhelming (in part because we may have the most confusing system of roads in America). And sure, it’s easy to get an initial feel for the area by checking out the shops in Faneuil Hall, getting some cheap eats in Allston, or seeing how the other half lives with a leisurely stroll down Newbury Street. There’s much more to Boston than this, however, and one of the best ways to see some of the most interesting parts of the city is to go a bit off the beaten path and start walking. There are countless options to do this, but the walks below should give you a little taste of what Boston has to offer.

Castle Island, South Boston

Back in the day, this is where Whitey Bulger apparently used to go to talk about… stuff, knowing that he would be safe in doing so. Today, this gorgeous harborside recreation area is where both locals and those in the know go to catch views of the Boston Harbor Islands and the city skyline while wolfing down hot dogs from Sullivan’s. Perhaps the best route to take is to start at the parking lot by Sully’s (or before if you’re taking the bus), walk on the causeway around the “Sugar Bowl,” loop back to Sullivan’s, grab some more hot dogs, then stroll around the fort area, taking in more views of the water.

[Directions: Red Line to Broadway, then City Point buses #9 or #11 will get you close to the loop.]

Arnold Arboretum, Jamaica Plain

Two hundred and seventy-five acres of open space might not sound like much, but when it’s in Boston—and when it’s full of hills, greenery, and water—it seems like a lot more, and this beautiful space near the end of the Orange Line has so much going for it that you could easily spend the better part of the day there. Rare trees and plants, three hills (including the very hidden Hemlock Hill), a moving stream, and a conifer forest that feels like something in the Pacific Northwest all make for a pleasant trip, and while you aren’t allowed to picnic there, it is a great place to kick back with a good book or set up a chair to get some sun if the weather is nice.

[Directions: Orange Line southbound to Forest Hills, then walk up South Street or the Arborway to any of the entrances.]

Charlestown Waterfront

Everyone seems to flock to the waterfront in downtown Boston or the Seaport District, but Charlestown, which sits on a peninsula just north of downtown, remains a bit under the radar even though the views there are every bit as good—and some of Boston’s most interesting history can be found here. By taking the Harborwalk (or the Freedom Trail) from downtown Boston over the Charlestown Bridge or the well-hidden walkway between North Station/TD Garden and the Charlestown Bridge, you can walk along the water for a mile or two, seeing such sites as the USS Constitution, the Navy Yard, and various piers that go far out into the water.

[Directions: Walk from North Station or Community College (on the Orange Line), or take bus #82 or #83 to City Square.]

Marlborough Street, Back Bay

Newbury Street can be fun—especially if you like to do a lot of people-watching and looking at things that you can never afford to buy—but paralleling it two blocks to the north is one of the great streets not just in Boston, but in all of New England if not America. Stretching from the Arlington Street and the Public Garden all the way to Charlesgate and the eastern edge of Kenmore Square, this tree-shaded mile-long road includes warm and comforting gas lamps, historic row houses, brick sidewalks, and an overall feeling of peace and quiet that makes it a good extension of the Beacon Hill walk mentioned above.

[Directions: From Boston Common, head west through the Public Garden to where Arlington Street and Marlborough Street meet.]

Neponset River Greenway, Dorchester

The southern border of Boston happens to be one of the city’s most scenic places, following the Neponset River from around Tenean Beach and the gas tank just off the Southeast Expressway all the way to Mattapan Square and beyond toward the Blue Hills in Milton. The part that is focused on here is the little section that leads west from Pope John Paul Park II and goes past grasslands that look like something out of the Midwest as it makes its way to Milton Landing, a cozy, hidden spot on the Milton/Dorchester line with park benches and great views of a harbor-like section of the river. From there, you can bike (or walk) for many miles, but the section mentioned above is particularly beautiful—and easy to do if you’re short of time. Oh, and don’t forget to wander around Lower Mills, a fascinating industrial area just north of Milton Landing that is on the National Register of Historic Places.

[Directions: From Ashmont station, take the Ashmont–Mattapan High Speed Line to Milton. (Note: This takes you to the end point of the above walk, at which point you walk east toward Pope John Paul Park II; if you have a car, start at Pope John Paul Park II, which is by the Neponset exit off the Expressway, and walk west.)]

Beacon Hill

While this charming neighborhood is basically in the heart of Boston, it is often overlooked, perhaps because it doesn’t have a ton of nightlife or food options. But if you like peace and quiet with a little bit of history mixed in, Beacon Hill is tough to beat. A good route might include some of the alleyways on the hill (Cedar Lane Way, Ridgeway Lane, and the secret path at the end of Smith Court, for example), along with stops at the uber-wealthy Louisburg Square and the hidden Phillips Street Park before dropping down to Charles Street where a handful of dining spots and stores await.

[Directions: Red Line to Charles or Park Street.]

South End and Bay Village

These two sections of Boston, which are mostly situated just south of the Back Bay, are sometimes overlooked or missed by newcomers to the city—which is a shame because the South End has a lot to see, including historic row houses, European-style residential parks and squares, and terrific restaurants and bars, while tiny Bay Village looks like a piece of Beacon Hill with its gas lamps and narrow lanes. Both neighborhoods are meant for walking, with a few highlights, including the picture-perfect Union Park and a peaceful and attractive section of the Southwest Corridor Park.

[Directions: Orange Line to Back Bay or Mass. Ave., or Green Line to Arlington or Copley.]

Emerald Necklace

Boston is full of parks and open spaces, and if you want to do a “walk to the sea” type of hike, you can basically do so by starting from Franklin Park in Roxbury or the Arnold Arboretum in Jamaica Plain, then following a route past Jamaica Pond, into the Fens, and along the Commonwealth Avenue Mall to the Public Garden and Boston Common. From there, you can do a short walk through downtown Boston to the waterfront, or you can take a very short walk from the Public Garden north to the Charles River and walk a whole lot more if so inclined.

[Directions: Orange Line southbound to Forest Hills.]

North End

Everyone knows the North End, with its strip of Italian restaurants and shops along Hanover Street and its slightly lesser-known strip along Salem Street, but some quiet and historic walks can also be done here. Narrow lanes, public alleys, and little parks can be found throughout if you look hard enough, with a few highlights being Charter Street park (and its very hidden alley down to Commercial Street), Powers Court, which is a tiny alley that looks like it hasn’t changed in 100 years, and the impossibly narrow Board Alley, which dead-ends at a basement bakery and an Italian food shop.  

[Directions: Walk east from the Haymarket subway stop.‎]

Harborwalk, South Station to Charlestown

We’ve saved one of the most interesting walks for last, and this one includes pieces of the Charlestown and North End walks above. Starting from South Station, you can walk along the east side of Fort Point Channel for memorable views of the Boston skyline, then cross the channel at one of the bridges, follow the Harborwalk north past Rowes Wharf and the aquarium, cut through Christopher Columbus Park into the North End, wind your way through various lanes and alleyways to a walkway over the water just west of the Charlestown Bridge, follow the Harborwalk signs into the Navy Yard, and wind your way past the piers and Spaulding Rehab to Building 114 on 16th Street, which you can access by picking up the phone and having the guard let you in, then kick back with food and drink from the vending machines in the little seating area while looking out the back door at the underside of the Mystic Tobin Bridge and Little Mystic Channel. Got that? Good. (Hint: Make sure you have a good map app on your phone.)

[Directions: Subway, bus, or train to South Station.]