The Ride Cafe

This route is a perfect family-friendly ride along the gorgeous Boston Harborwalk in Charlestown, over an impressive bike and pedestrian bridge to Cambridge Crossing, where you can watch duck boats, trains and drawbridges, oh my!

Ride highlights:

• The views of Boston, Boston Harbor, and the Charles River
• The comfortable and safe off-street paths along the Boston Harborwalk, The Freedom Trail, and the East Coast Greenway
• Many great parks and playgrounds
• Family friendly restaurants with tasty beer and food. All include spacious outdoor areas where you don’t have to worry about kiddos running into a busy street.

After my family and I relocated from Oakland, CA to Boston, we spent our initial nine months renting a quaint house in Charlestown. Built in the early 1800s, it stands as one of the oldest free-standing homes in the neighborhood. Beyond our affection for the house, the neighborhood itself is truly fantastic, and a multimodal enthusiast’s dream (provided one is able-bodied). The close nit streets and brick sidewalks bringing you up to the Bunker Hill Monument or down to Boston Harbor, are inviting at every turn. Conveniently, essential amenities such as the grocery store, CVS, Post Office, library, and bank were all within a quarter-mile radius. The Warren Tavern, frequented by Paul Revere, was just down the street. We were car-free when we moved to Boston, finding easy to navigate the area. When needed, we utilized a neighbor’s car through Getaround, sparing ourselves the hassle of parking and street-sweeping. (Stay tuned for a forthcoming post on the advantages of peer-to-peer car rental services like Getaround and Turo.)

We started biking with my daughter, Tatum, for the first time in Charlestown. At just 11 months old, we placed her in the green Ibert bike seat attached to the front of our bike. Over time, we gradually expanded our routes beyond our street to explore the Boston Harborwalk. Stretching across 43 miles along Boston’s shoreline, the Harborwalk intersects with sections of the Freedom Trail, the city’s renowned 2.5-mile path highlighting 16 nationally significant historic sites.

Since we rode this route almost every weekend, I wanted to make a map to share, because I felt 100% comfortable biking it with my 11-month-old. Since a majority of this route is on the Boston Harborwalk, it’s completely separated from cars, and the quarter mile of road with mixed traffic is a dead end, with a 25 mph speed limit (which people actually follow).

This route was designed to start and end at North Station, so those who don’t live in Boston could easily get in and out (and not have to pay for or deal with the hassle of parking). If you live along the Orange Line, take to Community College or North Station, since its much easier to get bikes on and off the subway compared to commuter rail, it has more frequent service, and it’s cheaper. When you get off at Community College, take a right along Gilmore Bridge, your first right down the sidewalk along the new buildings, and down the stairs (which have bike ramps), or the public elevator to Cambridge Crossing.

Bikes are allowed on the Orange Line anytime on the weekends, and during off-peak on weekdays. To learn more, check out Bringing Your Bike on the Train. Lastly, theres many other ways to get into Charlestown or East Cambridge, including the ferry, and some parking options on the Google map.

If you don’t have your own bike or would rather rent or use bike share, I’ve included Blue Bike stations on the map, and I recommend downloading the Blue Bikes app before starting your trip. Keep in mind the 30-minute time limit. For this leisurely ride with many stops, I recommend renting from Urban AdvenTours, which rents adult and kids bikes, They’re a walk away from North Station, or closer from Haymarket. Once you have your bikes, bike along the Atlantic Ave separated cycle track, back to the start of the route. All Urban AdvenTours rental bikes are also for sale. The price of a one day rental goes towards the purchase of your new bike, if desired.

If you’re close to Melrose, rent your family bike gear from The Ride Cafe. You can pick up and drop off rentals at the shop, at Oak Grove Station or a commuter rail stop.

If you start or end at North Station, the three things worth highlighting are:

• The Alcove Restaurant, which has great fire pits for non-summer season
• Night Shift Brewing, which just started serving coffee as well
• Row House, which if you came in for a bike ride with your kids, you most likely won’t be able take a rowing class, but keep it in mind for next time. This was my go-to studio for outdoor exercise classes during my time in Charlestown and I miss it oh-so-much!
• *All of these LoveJoy Wharf spots have great views of the Zakim Bridge.*

Once you cross the Locks from North Station, you’ll find a pretty great kids playground, called the Paul Revere Park Playground. The city put this in as a mitigation measure to the North Washington St Bridge construction. Next to the park is a great open grassy field, which can be a great picnic area.

After the kiddos get their energy out at the park, head into Charlestown along the Harborwalk. While biking along this route you’ll see Blackmoor Bar and Kitchen outdoor eating area to your left. It’s a nice spot to let the kiddos roam while you’re grabbing a bite or a drink. Head back onto the path and follow it along along the water and around Constitution Wharf, to see the USS Constitution.

I recommend stopping at The Anchor, Boston’s open-air wine and beer garden right on the Boston Harbor. The Anchor features games, books, and an outdoor piano for free public use. They had a kids pumpkin decorating event in October, and have other family-friendly events such as the Charlestown Navy Yard Scavenger Hunt and Family Ocean Day. There’s also bike parking and a bike pump out front, in case you need it.

Another noteworthy spot, just off the route, is Brewer’s Fork. During the spring season, their outdoor seating area is fully enclosed, offering peace of mind for parents concerned about children wandering into the street. Additionally, if it’s not crowded, they’re accommodating enough to allow you to bring your bikes into the back, as there’s unfortunately no bike parking available out front. While I’d suggest the Anchor for its stunning views and family-friendly atmosphere, I highly recommend Brewer’s Fork for its exceptional food and genuine neighborhood ambiance.neighborhood vibe.

The last point on the Charlestown-side of the route is Mayor Thomas M. Menino Park. The views are incredible, and there’s lots of places to sit while the kids run around. People come in from all over just to access this park, and you’ll have the best parking spot when arriving by bike. (Just bring your bikes into the park, like everyone else).

This is an in-and-out route, so take the easy and comfortable route back along the Harborwalk.

On the interactive Google Map, look for “What Typical Maps Don’t Tell You,” including public restrooms (found close to Pier 6 and where this photo was taken), as well as lovely picnic tables, ripe for a picnic spot.

Now for the Cambridge side! Head over the lovely North Bank Bridge and into Cambridge. At the top of the bridge, you’ll have a perfect vista point of not just Charlestown and the West End, but the Charles River and Cambridge as well. The Boston Duck Tour boats enter and exit the Charles just below the bridge, so it’s a good spot to slow down and hopefully catch this sight.

If your kids haven’t had enough park action, the North Point Playground is just at the foot of the bike/ped bridge. It has great water features during the summer, so have the kiddos bring their suits. The bike path to the “Common at CX” is quite lovely. This part of the path is less utilized than the Charlestown side, so this could be a great spot for beginners to practice riding.

If you need a coffee or treat, check out Cafe Beatrice, or The Lexington roof deck, for a full meal. The ground level patio is great for letting the kids run around, and it covered in case theres rain. Cafe Beatrice has a lovely fireplace for the chilly days.

Before you head back home, check out the Lynch Family Skatepark. The park is open from dawn to 9pm. Whether your kiddo(s) are skateboarding, biking or scootering, or just like watching the skatepark, like my daughter, this is an excellent use of activating public space under highways.

If you have any questions, don’t hesitate to reach out on Instagram @multimodalmom. If you do the route, we’d love to highlight your trip. Enjoy!

-Kara