Run Boston with a local

The must-run routes

• The Charles River paths (Esplanade / Dr. Paul Dudley White Path) — the flat path along the water on both the Boston and Cambridge sides, with bridges everywhere to build the distance you want.
• The Emerald Necklace — Olmsted's chain of parks, from Boston Common to the Arnold Arboretum, seven miles of near-continuous green across the city.
• Castle Island & Pleasure Bay (South Boston) — a flat ocean-facing loop around the bay, past Fort Independence with views over Boston Harbor.
• Jamaica Pond — a shaded 1.5-mile loop around the pond, rolling and popular, the go-to for Jamaica Plain runners.
• Boston Common, the Public Garden & Commonwealth Avenue Mall — the historic green lung and the tree-lined Back Bay promenade, flat and central, perfect for cruising in the heart of downtown.

Run like a local

Your guide isn't a service provider — they're a Bostonian who loves to run and wants to show you their city. They adjust the pace and distance to your level, pick the route to suit the time of day and the neighbourhood — the Charles River to cruise, the Emerald Necklace for the green, South Boston for the ocean — and share the Boston you won't find in guidebooks. Many of our guides here are running-club members and sports students from the city's campuses, who know their training loops by heart. You leave with a real memory — and often a GPX track to run again on your own.

Self-guided routes

Public, well-known routes you can run on your own — a solid plan B to get moving right away. But the best of TourMyRun is still discovering them with a local who takes you, at your pace.

• Charles River — Harvard Bridge / Longfellow Bridge loop≈ 2.8 miles (4.5 km), extend at will

  The great classic: run the Dr. Paul Dudley White Path on the Boston side, cross a bridge and come back on the Cambridge side. The Harvard–Longfellow loop is ~2.8 miles; chain the bridges (BU Bridge, River Street, Eliot) to stretch it to 5, 8 or 14 miles. Flat, car-free, skylines on both sides.

  Start : Charles River Esplanade, around Back Bay (Boston)

• The Emerald Necklace (Back Bay Fens → Jamaica Pond → Arnold Arboretum)≈ 5–7 miles depending on the stretch

  Olmsted's chain of parks threaded end to end: the Fens, the Riverway, Olmsted Park, Jamaica Pond, then the Arnold Arboretum. Almost all green, mostly flat, a nature escape in the heart of the city. Run it one-way (~5 mi to Jamaica Pond) or push on to the Arboretum.

  Start : Back Bay Fens, near the Museum of Fine Arts (Fenway)

• Castle Island & Pleasure Bay (South Boston)≈ 2.2 miles (3.5 km) loop

  A flat loop around Pleasure Bay linking Castle Island to the mainland by a causeway, facing Boston Harbor and the ocean. You pass the foot of Fort Independence. Wide, breezy, ideal at sunrise; stack laps for distance.

  Start : Castle Island / Pleasure Bay Beach, South Boston

• Jamaica Pond — the loop≈ 1.5 miles (2.5 km) loop

  The circuit around the pond on a rolling, shaded path, one of the links of the Emerald Necklace. A short, safe loop, perfect to repeat; a 5 km parkrun is run here every Saturday.

  Start : Jamaica Pond boathouse, Jamaica Plain

How it works

1. 1Search for a run in Boston and pick a slot that suits you (pace, duration, neighbourhood).
2. 2Book in seconds — the app handles booking, chat with your guide, the GPX track and payment.
3. 3Meet your guide at the meeting point and run. Zero logistics — lace up, we handle the rest.

Upcoming runs in Boston

• 
  14 km loop along the coast in Boston

  📍 marina, Boston · 59 min

• 
  Boston: 20 km loop along the coast

  📍 riverside path, Boston · 127 min

• 
  19 km loop along the coast in Boston

  📍 central station, Boston · 88 min

• 
  Boston: 13 km loop along the water

  📍 lakeside promenade, Boston · 70 min

FAQ — Running in Boston