Greenway + Trillium & TimeOut: Boston Bike Pairings

by Tegan

Like a wine pairing… on your bike!

After a brief Labor Day hiatus, (where we climbed our first 4000-footer in New Hampshire!) we are so excited to share with you the 4th installation in our Boston Bike Pairings series.

For those of you joining us for the first time this week, here’s the deal. A lot of people love pairing a certain cheese, fruit, or dish with wine, right? Well, we thought we’d add a little twist.

Over the course of the last few weeks, we’ve been releasing a series of what we’re calling “bike pairings.”

We introduce you to our favorite bike rides in Boston, with a twist. Each ride is mapped out to include a special treat: ice cream, doughnuts, breweries, and more. Enjoy!

This week’s pairing features the Emerald Necklace Greenway plus Trillium Brewing Company’s Fenway location and TimeOut Market. Make sure you check out the Fenway area (home to Fenway Stadium, where the Red Sox play) while you’re here, too!

Side note, if you’re interested in Fenway. check out this amazing guide by our friends at Itinerant Fan to all things Fenway! 

As we’ve mentioned previously– we are avid bikers, but don’t actually own our own bikes. 

How? We have an annual membership to Blue Bikes, which we super recommend for visitors to Boston! You can opt for a single ride, day pass, or month pass. Since we live here, we have the year pass, which costs us less than $10/month for unlimited 45-minute rides. 

(This is not an ad for Blue Bikes, btw, just the bike service we choose to use!) 

The Emerald Necklace is without a doubt one of Boston’s most gorgeous areas. As we mentioned in our Top 5 Boston Bike Rides post, a bike ride around the Emerald Necklace is great for those who want to feel like they’re surrounded by nature while still remaining in the city. It’s convenient to access, and a great way to explore a huge swath of the city.

Designed by legendary landscape architect Frederick Law Olmsted, the Emerald Necklace is comprised of 6 interconnected parks stretching from Brookline to Dorchester. 

For the purposes of this bike pairing, we’ll be focusing on 3 of them– the Fens, the Riverway, and Olmsted Park, which are all right next to each other, and connected by a unified greenway path for walking and biking. One of the reasons why this area is so great is that the bike path is almost entirely protected, with the exception of a few crosswalk areas. 

This route can be anywhere from an easy 4-or-so miles, to whatever length you’d like if you add on a loop around Jamaica Pond, the Fenway area, or Beacon Street. We’ve stretched this ride anywhere from 4 miles to 12. Here’s a map of a shorter loop, which came out to about 5 miles:

bike pairing greenway

You’ll pass beautiful ponds along the way, see lots of ducks and geese, and stay nice and cool underneath the shady tree cover. In the springtime, there’s lots of baby ducks and geese, as well as beautiful flowers in bloom.

Once you get to the end of the path, you’ll see the large 401 Park complex in front of you– a huge Brutalist structure that, while not beautiful by any means, contains lots of treats inside and nearby. 

Originally built in 1928 as a Sears-Roebuck distribution center, it was abandoned in the late 1980s and fell into disrepair. In the early 2000s, the area was revitalized with the addition of a movie theatre and office spaces, and today has a Target, hotels, and all sorts of other fun stuff to explore. 

bike pairing greenway

For this week’s treat, we have a double feature.

First off, inside 401 Park, you’ll find the TimeOut Market and food hall, which is a cavernous, enormous space filled with local restaurants, 2 bars, and snacks (including a Union Square Donuts stall, featured in our Brookline bike pairing!) There’s tons of communal seating (bench-style) in the middle, and is a great place to go with a group, so everyone picks what kind of food they’d like and can all sit together in the middle. 

Back outside, on what is known as “The Green,” you can’t miss Trillium Brewing Company‘s taproom. Trillium is a local brewery that is absolutely one of our favorites. They specialize in “hoppy”, “roasty,” and “sour/wild,” along with others seasonally. We really recommend the sour beers here, if that’s something you like! For a full list of their beers, see here

The current public art exhibition nearby, Grouping of Works from Fountain by Nicole Eisenman, is neat to look at, too, and there’s lots of green space to hang out in with your beer or snack from TimeOut. In the winter, there’s an ice skating rink, too! 

That’s it for #BostonBikePairing Week 4! See you next week! 

Remember to check out past bike pairings if you missed them, and let us know what you think in the comments!

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