The Route
Day 1: Boston to Milford, MA, 44 miles
Day 1 map
If you don't know Boston, take some time to visit downtown and Freedom Trail sites such as the Old State House and Boston Common, Faneuil Hall Marketplace and the Financial District and City Hall. It's a very walkable city, full of history and charm. While in the North End of Boston, make sure to get a cannoli at Modern or Mike’s Pastry.
Once you start biking, enjoy the Charles River Bike Path, which hums all day with fellow cyclists and runners and walkers and rollers. You'll head west from Boston and enter the western suburbs, including a stretch of the Mass Central Rail Trail that takes you from Weston to Wayland. From Wayland, you’ll turn south toward Framingham. If you are traveling between April and November, consider a short detour on residential neighborhood streets to the magical Native Plant Trust’s Garden in the Woods. This botanic garden showcases New England native plants in a beautiful natural setting. You can spend hours walking through the gardens. There are many lunch options to choose from in downtown Framingham, including wonderful Brazilian, Salvadoran and other small, locally owned grocery stores as well as the popular Jack’s Abbey Brewery. After Framingham, you’ll enjoy the extremely well-maintained soft-surface Upper Charles Trail/Holliston Rail trail, which is rideable on road tires. Along the Holliston rail trail, enjoy a smorgasbord of trail oriented businesses including a snack at the snack shop, Casey’s pub at the old train station, or coffee shop across the street just outside downtown. There’s also another trailside farmstand, built after the trail went in, Boston Honey Company that is another great option.
You’ll follow the trail to Milford, where there are multiple budget hotel options, north of downtown, and a few hotels are just off the trail. For dinner, downtown Milford includes some local restaurants and diners.
Day 2: Milford, MA, to Providence, RI, 37 miles
Day 2 map
You’ll head south from Milford on mostly quiet, residential roads. For lunch, 1.5 miles off route, downtown Bellingham has a few dining options. (Note that roads into and within downtown Bellingham are quite busy, with heavy, high-speed traffic volumes and limited shoulder/sidewalk.)
After Bellingham, you’ll continue to a short, shaded, beautiful stretch of the soft-surface Southern New England Trunk Line Trail. Keep an eye out for great wayfinding and trail art. Note that the trail is soft surface. The transition to the roadway from the current southern end of the trail is an unimproved side trail to MA-126 before the underpass that you might wish to walk. There are no curb cuts back onto the road.
From Blackstone, Massacusetts, you'll be riding along the Blackstone Valley, including more than 12 miles of the Blackstone River Bikeway from Woonsocket to Lincoln, Rhode Island. The area is part of the "cradle of the Industrial Revolution" — you'll enjoy views of historic mills and factories.
Providence is a handsome small city where the arts and new industry are thriving. Providence has also been rapidly building out on road, separated bicycle infrastructure in the last few years, with more coming soon. Book a hotel near downtown or check out Airbnbs downtown or on the East Side. Take a walk or ride through downtown and the striking campuses of Rhode Island School of Design and Brown University on the East Side. Close by, Geoff's has been serving superlative sandwiches, just as they claim, for decades. Sip a happy hour cold drink at the Hot Club on the Providence River. Great dining options abound. For a splurge and classic Providence dining experience, try Al Forno for grilled pizza and other artisan Italian dishes.
