top of page

Boston Urban Hike: The Greenway is for Everyone!

If you’re looking for a peaceful and delightful slice of the city of Boston, look no further than the Rose Kennedy Greenway! This 1.5 mile string of parks along Atlantic Avenue near the waterfront in Boston is the perfect way to spend a beautiful Sunday, and that’s exactly what we did-- we went on an urban wike!

Urban Hike Group on the Greenway

The Greenway essentially starts (or ends, depending how you look at it) at South Station. If you’re commuting into the city to spend the day on the Greenway, South Station is a great entry point. Similarly, the Greenway essentially ends (or begins) at North Station, another nice entry point. If you’re coming from Hingham or the south shore, take the ferry, which drops you off smack in the middle of the Greenway. Or, if you’re like me, drive down in the comfort of your own car and find parking.

Finding parking is usually a FUN (sarcasm) time in the city, but it’s often easiest on Sundays. I easily found free street parking on High Street near Congress Street, but there are plenty of nearby garages that will happily take your money and watch your car for you. You can find a list here.

When meeting up with friends, an easy meeting point is the exciting new Trillium Brewing Company Beer Garden, which opened this summer of 2017. Who doesn’t love drinking outdoors with friends on a beautiful day? If you’re a beer aficionado, you know Trillium to be one of the best breweries in the world. In fact, three of their beers (Congress Street, Melcher Street, and Summer Street) made the top 100 beers in the world according to the 2017 RateBeer Best Beer Awards. Grab a beer ($5-$11) and wait for your friends to arrive. If there’s a long line to enter, know that it usually moves quickly.

We found a comfortable spot at the picnic tables. I was a bit worried about the intense sun that day burning little Wike Baby’s new skin, but much of the beer garden is surprisingly shaded. After our group convened and caught up on the happenings of our lives, we were ready to explore the rest of the Greenway. If you’re hungry, you’ll notice many food trucks along the Greenway (here's a calendar of where to find them), besides restaurants along the street. Bon Me was parked outside of the beer garden when we visited, and the Cookie Monstah was a bit farther down by the carousel.

The Greenway is fully sidewalked, so it’s perfect for strollers. The sidewalks meander through each block, like a trail does in a forest. The gardens are carefully maintained by the Rose Kennedy Greenway Conservancy using sustainable practices—and they’re beautiful! It would be easy to find a peaceful spot among the gardens and relax with a book in hand. In fact, I did see some folks doing just that… but no time for sitting to read with baby on board!

As we walked, it was fun to think about the traffic in the tunnels just below us. You have to love the Greenway, but even if you somehow don’t, you have to love that it means the BIG DIG is over! Bostonians with any memory at all are so happy to look at this beautiful green space instead of the mess of I-93 hovering above the city. The Big Dig was conceived in 1983 with construction beginning in 1991 and lasting 15 years (about twice as long as expected). The Big Dig “megaproject” built the tunnel that routed I-93 under ground through the heart of Boston. Because the project took so long and caused so much traffic and construction noise, Bostonians felt like it would never end. But it did--and now it is not only functional but also provides for this beautiful new community green space!

Along the Greenway, we noticed a variety of interesting art installations. One such installation is the Harbor Fog water feature sculpture, which is a motion sensor-activated fog, light, and granite area that provides a sweet reprieve from the heat. Wike Baby enjoyed a little mist whilst sitting in her stroller… Mom did, too. Sometimes it’s nice to have a child around to give you an excuse to act like a kid!

Another interesting art installation is the striking black split dodecahedron sculpture and reflecting pool in the Armenian Heritage Park portion of the Greenway, which represents the immigrant experience. You’ll also see a labyrinth, representing life’s journey. This part of the park is dedicated to the victims of the Armenian Genocide.

Feeling like cooling off? Along the path, you’ll also find a few exhilarating water fountains perfect for children’s play. The Rings Fountain is near the Aquarium on Milk Street, and the North End Fountain is in the North End Park near Hanover Street. On this hot day, the fountains were full of kids anticipating the water’s next move!

Lots of Food Trucks on the Greenway

Near Long Wharf and Faneuil Hall, you’ll see the Boston Harbor Islands Pavilion with a custom carousel. This carousel was designed based on drawings by Boston school children. You can ride the whimsical New England creatures for $3 per person. Here’s also where we seriously considered purchasing ice cream from the food truck!

Right around the carousel is where you’ll also find the Artisans and Farmers Markets. The Artisans Market is supposed to be open on Saturdays 11am-5pm from May 6-October 28. The Farmers Market is open Tuesdays and Thursdays 11:30 am-6:30 pm from May 24-November 20. These are great places to find your next gift to give or pick up some supplies for dinner! Even though it was Sunday, the Artisans Market was bustling. You can find some beautiful and unique gift items there.

The Boston Zip Line

Near the Hard Rock Café, you’ll spot the Boston Zip Line, called “The Z”. You can’t miss it, but I have to say, it’s quite underwhelming! The zip line starts 30 feet in the air and takes riders on a 220 feet journey to the ground. Tickets are $8. I’d recommend it for adventurous children (must be 45 pounds and 40 inches tall).

If you start near Trillium Beer Garden and work your way to the North End Park and somehow avoid stopping at any of the food trucks along the way, you’ll probably be quite hungry. Perfect timing—the North End has some of the best food in the city!

Mike's Pastry from Hanover Street, someone is all tired out from our urban hike!

If you time your wike well, you can get to the North End in time for a dinner reservation. We didn’t have time for a meal, but we obviously had time to stop at Mike’s Pastry! I recommend picking up a cannoli and walking back to the North End Park portion of the Greenway to enjoy it.

The Greenway has something for everyone—all ages and interests. Bring your wike baby for a stroll, let your young child play in the water fountains, have your older child zip across the block on the Big Z, enjoy an ice cream sandwich from the food truck with your sweetie, shop for your mom, read a book, or even do some work utilizing the free wifi! Use the interactive map to plan your personalized urban wike.

No mater what you do at the Greenway… get outside together!

Have you visited the Greenway in Boston? What is the best feature of the Greenway in your opinion?

<<< Pin Me for Later! >>>

pin me

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites. The price doesn't change for you, it just enables us to get a small kickback.  We don't get paid to endorse products; opinions and reviews mentioned are completely our own. 



Spend time together with your family and friends exploring and adventuring.



Practice appreciating nature and your part in it.



Stay active and healthy.


Recenter yourself with peace and calmness.


Join the mailing list.

bottom of page