What is the Josh Billings?

The Josh Billings RunAground (often called the Josh Billings Road Race) is a beloved Berkshire triathlon: 27‑mile bike, 5‑mile paddle, and roughly a 6.4‑mile run that threads through Great Barrington, Stockbridge, and Lenox. The spirit is simple: to finish is to win.

Course snapshot

• Bike: Great Barrington start → handoff at Stockbridge Bowl.
• Paddle: 5‑mile lap on Stockbridge Bowl (kayak/canoe/SUP).
• Run: Around the lake to a finish at Tanglewood Main Gate.

For current maps and any updates, check the official site Course Maps.

When is it?

The event is typically held on a Sunday in mid‑September. For the latest confirmed date and schedule, see theRace Day and Schedule pages.

Where does it start and finish?

• Start: Great Barrington (bike start area per current‑year guidance).
• Finish: Tanglewood Main Gate in Lenox.

Bearings for race weekend: Tanglewood’s main entrance is about 1.4 miles west of Lenox Center on Route 183 (West Street).

As for proximity, Lee↔Lenox is roughly 4 miles by car, and Lee↔Stockbridge is roughly 6 miles. (Race‑day closures may affect timing.)

If you’re new to the area, Tanglewood visitor directions are here: Getting to Tanglewood.

Planning a quick stop: Canna Provisions Lee (closest & easiest)

Why Lee? Because you’re between Stockbridge Bowl and Lenox/Tanglewood with
convenient parking, fast pickup, and a deep menu. Get directions, hours, and the live menu:
Canna Provisions Lee, MA.

3‑step race‑day pickup

1. Pre‑order online from the Lee menu (beat any pre‑race rush).
2. Bring a valid 21+ ID.
3. Transport responsibly: keep sealed purchases in the trunk or a locked glove box while driving.

Coming from the south via I‑91 or swinging through after the Bash? Our Holyoke location is right off the corridor—ask a Lee budtender for directions.

Race‑day cannabis rules (know before you go)

• No public consumption. Massachusetts prohibits consuming cannabis in public places; civil penalty up to $100. Event guidance also prohibits smoking in Tanglewood lots and on the beach.
• No open container in vehicles. An “open container” (broken seal/partially consumed) is not allowed in the passenger area. Keep it in the trunk or a locked glove box; fines up to $500.
• Do not drive impaired. Operating a vehicle under the influence of cannabis is illegal. Plan a designated driver or rideshare after the Bash.

This is general information—not legal advice. Always follow posted event rules and Massachusetts law.

Spectator snapshot & local tips

• Arrive early in spectating zones—some roads toward the Bowl close in the morning, and parking is controlled near Tanglewood.
• Best vibe: the finish at Tanglewood Main Gate—it’s where friends and family cheer runners home.
• Pack smart: sun protection, layers, portable chair, cash/card, water, and odor‑proof storage for any purchases (kept sealed and stored properly while driving).

Why the Josh Billings Road Race (RunAground) matters

The Josh is a community tradition and a 501(c)(3) event that donates proceeds to the Berkshire United Way.

FAQ