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My Votes for the Best Family Boston Bike Trails & Treats!

14 items

Sarah Winter Whelan

I've been on a mission to get more family together time in a way that helps us be active and not on our screens! It can be hard to find something that pleases both the kid in high school and the one in elementary school. I've found BIKING (and ice cr...

Sections

Neponset Greenway & Lazy Bear Ice Cream

Holliston Rail Trail & Treats

Cochituate Rail Trail & The BEST ice cream and coffee west of 95!

The Emerald Necklace

Neponset Greenway & Lazy Bear Ice Cream

First up is the Neponset Greenway and delicious ice cream in the city! Starting by parking at Pope John Paul II Park in Dorchester. There's a big parking lot, a playground, and you can walk or bike along the paths that abut the Neponset River. If you... to Mattapan's Blue Hill Ave (and even beyond). Afterward, drive a short mile to Lazy Bear Creamery. I highly recommend Salty Sloth and Twisty Tree (and the kids will love the swing seats!).

A great rail trail inside city limits along the banks of the Neponset River! We started by parking at the Pope John Paul II Park parking lot and heading west up the river toward Mattapan. We got to Blue Hill Ave and turned back, but you can actually ...

Neponset Greenway Trail (In Boston)

This ice cream spot near the Neponset Greenway Trail is the best way to wrap up a ride!

Lazy Bear Creamery, Dorchester

Even if you don't bike, this Park has a gorgeous set of paths for strolling along the Neponset River

Pope John Paul II Park in Dorchester

Holliston Rail Trail & Treats

Next up is the Holliston Rail Trail, a gorgeous, scenic, sun-dappled trail. We first grabbed sandwiches from Olivia's Market. 10/10 - no notes. Then we drove to the “Upper Charles Trail Parking” in Milford off E Main Street behind Prezzo Grille and B...

This was an awesome rail trail. It had paved and gravel portions, went through wooded areas, past Willow Brook Horse Farm, and great spots along the way!

Holliston Rail Trail

Great spot for coffee, bagels, or pastries!!

Coffee Haven by Blue Moon

Somewhere we would have stopped if they'd been open! It looks so cute.

Boston Honey Company

A delicious spot to grab sandwiches before (or after) the bike ride!

Oliva’s Market

Cochituate Rail Trail & The BEST ice cream and coffee west of 95!

This is a super family friendly, easy bike path along the towns of Natick and Framingham. The CRT is a 3.7-mile paved path. The path takes you along Lake Cochituate, where you can view kayakers and paddle boarders. It has a lot of parking right at th...

A lovely, easy, multi-use paved trail.

Cochituate Rail Trail

Best ice cream I've had in awhile and iced mocha. Definitely recommend the salted caramel and pretzel or cookie monster ice cream.

Wagon Creamery

The Emerald Necklace

The Emerald Necklace is Boston's Network of green space across several neighborhoods. You can bike, walk, run from Franklin Park to the Public Garden. There are so many spots to explore! One of my favorite sections is path that stretches from Jamaica...

The Emerald Necklace spans across the city with many segments to explore whether on foot or bike.

Map of the Emerald Necklace

This is the organization that helps ensure the importance and stewardship of the parks.

The Emerald Necklace Conservancy

During the summer months, this area of the Necklace has installations by local artists. They're always incredible and thought-provoking.

Riverway Path (between Brookline Ave and Fenway) and Studios without Walls

Just off the Necklace in JP is, of course, J.P. Licks. The best ice cream in the city!

J.P. Licks Ice Cream

Right next to the entrance there is FREE, monitored bike parking. Making this the an incredibly awesome way to get to and from the Park.

FREE Bike Parking at Fenway Park