Short routes (under 3 miles)
These routes are the perfect length for beginners, day-drinkers, and the perpetually winded.
1. Public Garden and Boston Common
A loop around the perimeter of these adjacent parks is about a mile and a half long. You’ll get to cross the world’s smallest suspension bridge, get a glimpse of the State House and the gorgeous Federalist-style buildings on Beacon Hill, and trot along the Freedom Trail for a minute. In the afternoon, you can spot cult-like groups of maniacally grinning people twerking en masse or slowly fighting invisible ninjas in the Common.
If you want to incorporate a little speed workout into your routine, just venture too close to a swan. It’ll chase you halfway around the park, gnashing its creepy little tooth razors at you while making a sound like an elephant stepping on a kazoo. If you get overwhelmed by your athletic moves, refuel with food-truck fried dough and marvel at its similarity to your pasty thigh. Maybe those $50 ultramarathon-grade spandex shorty shorts weren’t the best choice at this early stage in your exercise regimen. Moving on!
2. Charles River from the Mass Ave to Longfellow Bridges
This route covers about three miles along the river. You’ll get to heave by Back Bay on the Boston side before crossing the Mass Ave Bridge to Cambridge. As you cruise by Central and Kendall Squares, you’ll have the opportunity to fart in the general direction of all the MIT dweebs and pretentious hipsters skulking along in their skinny jeans and lipliner-enhanced frowns.
For a beer break, stop at the Cambridge Brewing Company and sip a locally brewed Spring Training IPA. They have an outdoor patio, so the summer breeze will carry your exercise musk away. Refreshed, proceed to the Longfellow Bridge, fart at all the fancy doctors at Mass General, and head along the river until you’re back where you started.
3. Jamaica Pond
This is another mile-and-a-half route, and well worth the trip down to JP, a neighborhood that’s often overlooked by visitors to Boston. Hop on the 39 bus to South Huntington St or take the Orange Line to Stony Brook, and it’s a short walk (or jog!) from either.
The Pond’s smooth, placid water is surrounded by weeping willows, and you can rent a kayak, rowboat, or sailboat here too. Enjoy plentiful opportunities for parkouring around couples getting engagement photos. People fish in the pond, and I once saw a (potentially high and/or drunk) person rip all his clothes off and leap screaming into the water, so you could try some aquatic cross-training if you’re feeling adventurous.
Medium routes (4-7 miles)
4. Jamaica Pond to the Arboretum
If you’ve finished your run around the Pond and you’re still feeling fresh, continue on to the Arnold Arboretum. Just jog down the Arborway and you’ll be there in no time. This 281-acre hilly landscape is full of manicured gardens, quiet meadows, and shallow streams.
You’ll almost definitely get lost in here, so bring a snack, a book, and maybe a sketchpad in your running backpack. And watch out for nudists (slightly NSFW)! Those JP hipsters can get a little too artsy sometimes.
5. The Harborwalk
As its name so eloquently implies, this walkway runs all along the Boston Harbor. Even though it’s not called the Harborwheeze, I encourage you to slow-jog it. If you start at Rowes Wharf and double back once you hit the bridge to Charlestown, you’ll cover six miles.
This takes you by several delicious seafood spots on the waterfront — try the Boston Sail Loft for delicious clam chowder and a great view of the Harbor. You can also make a pit stop at Mike’s Pastry in the North End for a pyloric-valve-destroying array of cannoli options before staggering to the Black Rose or the Littlest Bar in the Financial District for your end-of-run celebratory vat of Guinness. If you follow the Freedom Trail across the bridge and run back, you’ll hit eight miles.
The waterfront area of Charlestown is nothing like The Town would have you believe. You can check out the USS Constitution in the Navy Yard before galumphing down tree-lined streets to the Bunker Hill Memorial.
Long runs (over 8 miles)
If you’re trying to run over eight miles, I think you’re getting uncomfortably aggressive. I recommend bringing a water belt, map of all available toilets on your route, and smelling salts in the likely event you get the vapors and need to be revived.
The best way to accomplish this slow train to your own destruction is to knit together a few of the above runs. Most are part of the Emerald Necklace, which is a fairly seamless park system that runs through the city. Be sure to stop at all the bars and restaurants, or you may die of starvation and excessive sobriety.
May you sear retinas with your hot new beach bod.