Sample the best of southern New England. From Boston, travel west and south to Providence, R.I., down the Narragansett Bay and east to Cape Cod, then ferry back to Boston.
Day 1: Boston to Worcester, MA, 50 miles.
If you don't know Boston, take some time to visit the 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.
Once you start biking, enjoy the Charles River Bike Path, which hums all day with fellow cyclists and runners and walkers. 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. Ride along Lake Quinsigamond, home to rowing championships, before ending in downtown Worcester. You'll find a number of reasonable hotels around Main Street, close to the Greenway. Thirsty? Locals recommend a cold Be Hoppy at Wormtown Brewery. You'll find beer AND food just up the street at Brew City Grill and Brew House.
Day 2: Worcester, MA, to Providence, RI, 57 miles
You'll be riding along the Blackstone Valley today, 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. 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 about. 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, 45 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. Picnic at one of the parks along the river and take advantage of air-conditioned bathrooms at the history center near the anchored battleships. The road gets quieter after Fall River before ending in the historic whaling town of 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 Hyannis, MA, 57 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. You'll ride along the coast through Craigville Beach before hitting Hyannis, where you can find motels, B & Bs, Airbnb, or a hostel .
Day 5: Hyannis to Provincetown, MA, 56 miles
Enjoy coastal views riding out of town before hitting the scenic Cape Cod Rail Trail just out of South Dennis. The 22-mile bike path winds through Harwich, Brewster (with a detour through Nickerson State Park), Orleans (through the beautiful Rock Harbor area) and continues through a salt marsh to the Cape Cod National Seashore Center in Eastham and Le Count Hollow in Wellfleet.
At 20 miles, stop at Eat Cake 4 Breakfast just off the trail in East Brewster for a rest stop treat, around the corner from a bike shop if you need it. Enjoy a gorgeous coastal road taking you to Provincetown, where you can wheel your bike onto the fast ferry ride back to Boston.
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