There are 4 ways to get from Gloucester to Winthrop by train, bus, car, or taxi
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train
best- Take the train from Gloucester to Chelseatrain Newburyport/Rockport Line
1h 40m$10–24Line 7 bus, line 436 bus
cheapest- Take the bus from Main St & Pleasant St to Northshore Mall At JC Penney Entrancebus 7
- Take the bus from Northshore Mall @ Entrance F to Lynnbus 436 / ...
3h 21m$6–14Drive 29.3 mi
- Drive from Gloucester to Winthropcar 29.3 mi
43 min$6–8Taxi
- Take the taxi from Gloucester to Winthroptaxi 29.3 mi
43 min$90–110
Gloucester to Winthrop by train, bus, and subway
Questions & Answers
The cheapest way to get from Gloucester to Winthrop is to drive which costs $5 - $8 and takes 43 min.
The fastest way to get from Gloucester to Winthrop is to drive which takes 43 min and costs $5 - $8.
No, there is no direct bus from Gloucester to Winthrop. However, there are services departing from Main St & Pleasant St and arriving at Pauline St opp Woodside Ave via Northshore Mall @ Entrance F, Lynn and Orient Heights. The journey, including transfers, takes approximately 3h 21m.
No, there is no direct train from Gloucester to Winthrop. However, there are services departing from Gloucester and arriving at Orient Heights via Airport. The journey, including transfers, takes approximately 1h 40m.
The distance between Gloucester and Winthrop is 33 miles. The road distance is 29.5 miles.
The best way to get from Gloucester to Winthrop without a car is to train which takes 1h 40m and costs $10 - $24.
It takes approximately 1h 40m to get from Gloucester to Winthrop, including transfers.
Gloucester to Winthrop bus services, operated by Cape Ann Transportation, depart from Main St & Pleasant St station.
Gloucester to Winthrop train services, operated by MBTA, depart from Gloucester station.
The best way to get from Gloucester to Winthrop is to train which takes 1h 40m and costs $10 - $24. Alternatively, you can line 7 bus and line 436 bus, which costs $6 - $15 and takes 3h 21m.
What companies run services between Gloucester, MA, USA and Winthrop, MA, USA?
MBTA operates a train from Gloucester to Chelsea hourly. Tickets cost $5–11 and the journey takes 52 min. Alternatively, you can take a bus from Main St & Pleasant St to Pauline St opp Woodside Ave via Northshore Mall At JC Penney Entrance, Northshore Mall @ Entrance F, Lynn, Wonderland, Wonderland, Orient Heights, and Orient Heights in around 3h 21m.
Train from Gloucester to Chelsea
- Ave. Duration
- 52 min
- Frequency
- Hourly
- Estimated price
- $5–11
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $5–11
- Phone
- +1 978 283 7916
- [email protected]
- Website
- Cape Ann Transportation
Bus from Main St & Pleasant St to Northshore Mall At JC Penney Entrance
- Ave. Duration
- 41 min
- Frequency
- 5 times a week
- Website
- Cape Ann Transportation
Bus from Northshore Mall @ Entrance F to Lynn
- Ave. Duration
- 48 min
- Frequency
- Hourly
- Estimated price
- $1–5
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Ave. Duration
- 43 min
- Estimated price
- $90–110
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More Questions & Answers
Gloucester to Winthrop bus services, operated by Cape Ann Transportation, arrive at Northshore Mall At JC Penney Entrance station.
Gloucester to Winthrop train services, operated by MBTA, arrive at Chelsea station.
Yes, the driving distance between Gloucester to Winthrop is 30 miles. It takes approximately 43 min to drive from Gloucester to Winthrop.
There are 1479+ hotels available in Winthrop.








