Speedrun
One Saturday. Five stops.
The fastest 250 XP in Boston. Go in order, all on foot.
- 1Boston Common
- 2State House dome
- 3Faneuil Hall grasshopper
- 4Paul Revere House
- 5Cannoli on Hanover
01 · The routes
Six routes. Pick one.
Two are live. Four drop this fall. Every one starts at a T stop.
Freedom Trail challenge
All 16 stops on the red line, Common to Bunker Hill. Find the grasshopper on Faneuil Hall, skip the paid houses, finish with a cannoli.
Boston city game
Four short loops: Downtown, Beacon Hill and Back Bay, the Seaport, Cambridge. Good for a group that argues about where to eat.
North End food crawl
Pizza, pasta, cannoli, espresso. In that order. Mike's vs Modern gets settled here.
Chinatown dumpling crawl
Start at the gate on Beach Street. Soup dumplings, bubble tea, egg tarts, then noodles if you still have room.
Boston photo challenge
A shot list, not a route. Acorn Street, the purple windows, the Zakim from the North Point bridge.
Bar crawl, self-guided
Five bars, one walkable loop, no one yelling into a megaphone. XP works at the bar.
02 · How it works
Walk. Snap. Spend.
Pick a route.
Six to choose from. Each starts at a T stop, so no car and no parking.
Snap each stop.
Take a photo when you get there. The app checks you found the right thing.
Spend the XP.
Every stop pays out. Cash it in at partner cafes and bars around the city.
03 · Rewards
Turn your adventure into currency.
XP unlocks tiers. Tiers unlock rewards at partner spots like Cardullo's, Tikki Rock and Don't Tell Aunty.
Off the couch
Your first reward: a small freebie at a partner cafe or bar.
Knows a guy
Bigger rewards at partner spots, plus a badge on your profile.
Boston, beaten
Every route on this page done. Top-tier rewards and bragging rights.
04 · Tour or challenge
Skip the $40 tour.
Guided city games are fine for an office outing. For everything else, a challenge is cheaper and runs on your schedule.
| Guided tour | Challenge | |
|---|---|---|
| Cost | $20–$40 a head | Free, and it pays you back |
| Start | Fixed times, book ahead | Whenever you show up |
| Pace | About 2 hours, no lunch | Yours. Take the long lunch. |
| Where | Mostly Downtown | Six neighborhoods |
| Again? | Pay again | Six routes. Do them all. |
05 · Make your own
Four rules for a good route.
Stay in one neighborhood.
Or two that touch. Downtown to Harvard loses 30 minutes on the Red Line.
Make stops specific.
"Faneuil Hall" is a place. "The gold grasshopper on top" is a stop.
Feed people.
One food stop every four or five landmarks. Pick a partner spot and get more XP and perks.
Check the clock.
Burying grounds close at dusk. Downtown is best early, the Seaport at sunset.
FAQ
Got questions.
What is a Boston challenge?
A challenge is a self-guided route through Boston with a list of real stops in walking order. You start whenever you like, walk at your own pace, and snap a photo at each stop. No guide, no fixed start time, nothing to buy. In the app, each challenge tracks your stops and pays out XP as you go.
What does XP get me?
XP unlocks reward tiers redeemable at partner cafes, bars and dessert spots around Boston, including Cardullo's, Tikki Rock and Don't Tell Aunty. 500 XP gets your first small freebie, 1,500 XP unlocks bigger rewards plus a profile badge, and 4,800 XP unlocks top-tier rewards.
Do I need the app?
No. Every route is published here with real addresses, T stops and directions, so you can walk it straight from the page. The app is what turns your photos into XP: it checks each stop, tracks your progress, and lets you spend what you earn at partner spots.
How long does a route take?
Most routes run 90 minutes to 2 hours. The Freedom Trail challenge is the longest at 3 to 4 hours because it covers 2.5 miles and 16 stops. The five-stop speedrun is the fastest way to bank 250 XP in under an hour.
Can I bring kids?
Yes. The Freedom Trail challenge and the Downtown leg of the city game are flat, stroller-friendly and full of things to spot: the gold State House dome, the red line in the sidewalk, the grasshopper weathervane on Faneuil Hall. Keep it to a couple of miles and add a snack stop.
Which Freedom Trail stops cost money?
Most of the 16 stops are free to view from outside, which is all the challenge requires. The Old State House, the Paul Revere House and the Old South Meeting House charge admission if you want to go inside; skip them and the route still counts.
Where was the Boston Massacre?
At the corner of State and Congress Streets, marked by a cobblestone ring set into the sidewalk outside the Old State House. It's stop 8 on the Freedom Trail challenge.
Why is there a grasshopper on Faneuil Hall?
The copper grasshopper weathervane has topped Faneuil Hall since 1742, modeled after the one on London's Royal Exchange. It became an informal test of loyalty during the Revolution: ask a stranger what's on top of Faneuil Hall, and if they didn't know, you knew they weren't from Boston.
What's the oldest thing on the routes?
King's Chapel Burying Ground, dating to 1630, on the Freedom Trail challenge. It's the oldest burying ground in the city, older than the chapel itself.
Why does Chinatown have a gate?
The paifang gate on Beach Street was a 1982 gift from Taipei, marking the neighborhood's main entrance. It's the starting stop on the Chinatown dumpling crawl.