Boston Weekender
Not ready for a four-day journey through Massachusetts, Maine, and New Hampshire? We got you covered. This trip takes routes from the best of the Boston & Maine Eastern and Northern Lines and smashes them together into one wonderful weekend adventure in Beantown.
Ride Details
103 miles
2 day ride
Depart: Amtrak Northeast Regional
Penn Station >> Boston
Return: Amtrak Northeast Regional
Boston >> Penn Station
Mostly asphalt with some crushed stone
Stay in Boston
Maybe you’re short on time. Maybe you’re just dipping your toe into this bike tripping thing and not ready to commit to a couple hundred miles in the saddle across state lines. Or maybe, just maybe you’re the oddball New Yorker that really just loves Boston and its people. Whatever the rationale, this trip is for you. A solid two-day jaunt from Lexington and Concord and up the North Shore to Salem.
If you get inspired after this one, consider venturing further afield via the Boston & Maine Eastern Line or Northern Line trips. They don’t disappoint!
Day 1: Boston <> Concord
Check out Bedford. The Minuteman Commuter Bikeway lives up to its name and is a straight shot that gets you out of Boston in no time to the end of the trail in Bedford. The Bedford Depot and Depot Park are worth a stop, with their cool old Boston & Maine rail cars and other fodder for bike selfies.
Send it on the Reformatory Branch Trail. This short heavily wooded trail between Bedford and Concord is a world of fun. Ride it fast and enjoy! Take a quick break to marvel at the beauty of the Great Meadows National Wildlife Refuge on the way.
Visit North Bridge. Concord’s North Bridge is where the American Revolution began, the site of the “shots heard round the world” where the colonial militiamen first exchanged gunfire with British soldiers. Part of Minute Man National Historical Park, the area surrounding the bridge is beautiful and full of history.
Eat in Concord. No shortage of places on Main Street. Try Main Street Market & Cafe, Sally Anns Bakery & Food Shop, Haute Coffee, or Helene’s Restaurant.
Explore Minute Man National Historic Park. After North Bridge, the rest of the park follows the old road between Lexington and Concord, now called Battle Road Trail. It’s a real experience that genuinely feels like riding back in time. Stop to read the informative signs and take some bike selfies along the way. Take your time and enjoy.
Don’t miss Lexington. Battle Road Trail spits you out a short mile and a half from the Lexington Common National Historic Site. Take some time to explore here as well.
Single track anyone? Determined to stay as much as possible on trails, I ended up on some pretty gnarly mountain biking trails that pick up south of Lexington and end just north of Waltham. My steel frame touring bike with 28mm tires was the wrong bike for the job. Had I had my gravel bike on the other hand… these trails would have been a hell of a lot of fun. If you’re up for it, pick up the Brookhaven Nature Trail at Brookhaven At Lexington and follow that south along the Western Greenway to The Robert Treat Paine Estate. Google Maps is your friend here, just follow the dotted green line.
Bike the Charles. Watching the skyline slowly rise along the Charles River Bike Path makes for a nice approach.
Enjoy Boston. You’ll practically ride right past Harvard Square. Take a quick trip to Harvard Yard and take a bike selfie in front of the John Harvard Statue while you’re there. Hit up Raven Used Books if you need a train read. Roll through Public Garden and Boston Common. Cap it off with a pie at Regina Pizzeria or wherever else suits your fancy.
Day 2: Boston <> Salem
Start with a little history. Heading north out of Boston you’ll pass through Charlestown, which is the oldest neighborhood in Boston. Take a few to visit Paul Revere’s Ride, Boston National Historic Park (home to the USS Constitution), and Bunker Hill. They make for some nice sights to get you through the not particularly appealing suburbs that follow on the north side of the Mystic River. They also make good spots for bike selfies.
Take a detour to Nahant. It’s a completely unnecessary detour, but oh so worthwhile. Nahant is a strikingly beautiful spit of land that has no business being a peninsula. It’s effectively an island you can bike to, thanks to the sand-flanked causeway that connects it to the mainland, otherwise known as Nahant Beach. Do a loop of the island (watch out, it’s hilly!) and be sure to see Lodge Park, East Point Loop Station, Forty Steps, and Canoe Beach.
Hit the beach! And you’ll pass plenty of them! Nearly two dozen beaches line the shores between the southern tip of Nahant and Marblehead. In addition to Nahant Beach, you’ll find King’s Beach, Preston Beach, and Devereux Beach, just to name a few of the bigger ones. Personally, I was a fan of Fort Beach in Marblehead, because it’s more of a swimming cove than a big sandy touristed beach.
See the Salem witches. More specifically, see the Salem Witch Trials Memorial. It’s a sobering tribute to a period of historical insanity. There’s plenty of other less serious witch kitsch in town, if that’s your thing. For maritime history buffs, don’t miss the Salem Maritime National Historic Site.
Eat in Salem. I recommend Clam Shack if you’re looking for lobster rolls. Watch out for the seagulls. They’re like Washington Square Park squirrels with wings. You’ve been warned. Plenty of other eats all over Salem too.
Check out Winter Island Park. For what will appear in photos as an abandoned Coast Guard air station overrun by RVs, is actually a surprisingly cool campground and park. Waikiki Beach is a delightful swimming hole and the park bench next to the harbormaster has a great view of the harbor.
Follow 1A back down the coast. The stretch from Salem to Lynn is nothing grand, but it’s worth the ride along Revere Beach that follows before bringing you back into Beantown.
