Sample the best of southern New England. From Boston, travel south to Providence, R.I., down the Narragansett Bay and east to Cape Cod, then ferry back to Boston.
Day 1: Boston to Milford, MA, 44 miles
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
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.
Day 3: Providence, RI, to New Bedford, MA, 51 miles
Enjoy the beautifully scenic (but popular, so possibly crowded) East Bay Bike Path from India Point Park in Providence to Warren along the Narragansett Bay. A few coffee shops and other amenities are located on or a block from the trail if needed. It's a little sad to turn off the path in Warren to head east, so cheer yourself up at the turn with a classic Rhode Island treat: Del's Frozen Lemonade, 65 Child Street in Warren.
You'll cross a nicely protected bike-ped bridge over the Taunton River into Fall River. For lunch on the way into town, you could picnic at one of the parks along the river and take advantage of air-conditioned bathrooms at the history center near the anchored battleships. If you like pierogi’s ride all the way into downtown and try Patti’s Pierogis for lunch. Outside Fall River, you ride along quiet small roads that take you into the historic whaling city of New Bedford. You can learn more of the history the New Bedford Whaling Museum and New Bedford Whaling National Historic Park. Make sure to pause and take in the views on the Hurricane Barriers in New Bedford. Book a room at New Bedford Harbor Hotel and walk to Moby Dick Brewing Co. for dinner, cold brews and a touch of whaling history.
Day 4: New Bedford to Brewster, MA, 69 miles
Enjoy a stretch of greenway in Fairhaven, just across the bridge from New Bedford, before hitting the shoulders of slightly busy roads. Further north, the Cape Cod Canal bike path offers 7 miles of delightful trail before you walk your bike over the Sagamore Bridge and onto the Cape. Charming town centers such as Sandwich offer places to, well, order sandwiches.
Enjoy coastal views riding out of town before hitting the scenic Cape Cod Rail Trail just out of South Dennis. The flat, 25 mile Cape Cod Rail Trail winds from South Yarmouth to South Wellfleet. The 6 Cape Cod towns along the rail trail offer many shops, restaurants, and vacation rentals and accommodations. Consider a longer day of mileage to camp at Nickerson State Park in Brewster and enjoy the sandy bottomed pond for swimming and a DCR Campground right on the trail. Note that the campground’s general store sells ice cream bars and popsicles.
Day 5: Brewster to Provincetown, MA, 35 miles
From Brewster, the Cape Cod Rail Trail continues to Orleans (through the beautiful Rock Harbor area) and on through a salt marsh to the Cape Cod National Seashore Center in Eastham and Le Count Hollow in Wellfleet.
Stop at Eat Cake 4 Breakfast Bakery just off the trail in East Brewster for breakfast, around the corner from a bike shop if you need it. Or enjoy a taste of France at PB Boulangerie in South Welfleet.
Just before Provincetown, stop at Jam’s/the Truro General Store in Truro for a sandwich for lunch and enjoy a picnic in the park across the street. Enjoy a gorgeous coastal road taking you to Provincetown. Before you can wheel your bike onto the ferry ride back to Boston, take time to enjoy the shops, restaurants and crowds in Provincetown. More information on the ferries available at https://www.provincetown-ma.gov/751/Ferries
If you have extra time, ride on the trail to Race Point Beach and stop for a swim. And if you just don’t want to leave, consider a few nights camping at the Trustees’ Dunes’ Edge Campground. (Note they have a two night minimum stay.)
Recommended by Molly Henry with updates from Allison Burson and Kristine Keeney
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