There are 5 ways to get from Dorchester to Winchester by subway, train, bus, taxi, or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Subway, train
best- Take the subway from Jackson Square to North Stationsubway Orange Line
- Take the train from North Station to Winchester Centertrain Lowell Line
1h 8m$3–9Subway, line 134 bus
- Take the subway from Ruggles to Wellingtonsubway Orange Line
- Take the bus from Wellington to Laraway Rd @ Winchester Ctrbus 134
1h 11m$3–7Line 23 bus, subway, line 134 bus
- Take the bus from Washington St opp Algonquin St to Rugglesbus 23
- Take the subway from Ruggles to Wellingtonsubway
- Take the bus from Wellington to Laraway Rd @ Winchester Ctrbus 134
1h 43m$6–12Taxi
- Take the taxi from Dorchester to Winchestertaxi 13.5 mi
23 min$40–55Drive 13.5 mi
- Drive from Dorchester to Winchestercar 13.5 mi
23 min$3–4
Dorchester to Winchester by subway and train
Questions & Answers
The cheapest way to get from Dorchester to Winchester is to drive which costs $2 - $4 and takes 23 min.
The fastest way to get from Dorchester to Winchester is to taxi which takes 23 min and costs $40 - $55.
No, there is no direct train from Dorchester to Winchester. However, there are services departing from Jackson Square and arriving at Winchester Center via North Station. The journey, including transfers, takes approximately 1h 8m.
The distance between Dorchester and Winchester is 12 miles. The road distance is 13.6 miles.
The best way to get from Dorchester to Winchester without a car is to subway and train which takes 1h 8m and costs $3 - $10.
It takes approximately 1h 8m to get from Dorchester to Winchester, including transfers.
Dorchester to Winchester train services, operated by MBTA, depart from Jackson Square station.
Dorchester to Winchester train services, operated by MBTA, arrive at North Station.
Yes, the driving distance between Dorchester to Winchester is 14 miles. It takes approximately 23 min to drive from Dorchester to Winchester.
There are 1656+ hotels available in Winchester.
What companies run services between Dorchester, MA, USA and Winchester, MA, USA?
There is no direct connection from Dorchester to Winchester. However, you can take the subway to North Station, walk to North Station, then take the train to Winchester Center. Alternatively, you can take a subway from Ruggles to Laraway Rd @ Winchester Ctr via Wellington and Wellington in around 1h 11m.
Subway from Jackson Square to North Station
- Ave. Duration
- 15 min
- Frequency
- Every 10 minutes
- Estimated price
- $3
- Website
- MBTA - Massachusetts Bay Transportation Authority
- Schedules at
- Subway Schedules
- Adult
- $3
Train from North Station to Winchester Center
- Ave. Duration
- 16 min
- Frequency
- Hourly
- Estimated price
- $1–7
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $1–7
Subway from Ruggles to Wellington
- Ave. Duration
- 19 min
- Frequency
- Every 10 minutes
- Estimated price
- $3
- Website
- MBTA - Massachusetts Bay Transportation Authority
- Schedules at
- Subway Schedules
- Adult
- $3
Subway from Ruggles to Wellington
- Ave. Duration
- 19 min
- Frequency
- Every 10 minutes
- Estimated price
- $3
- Website
- MBTA - Massachusetts Bay Transportation Authority
- Schedules at
- Subway Schedules
- Adult
- $3
Bus from Wellington to Laraway Rd @ Winchester Ctr
- Ave. Duration
- 19 min
- Frequency
- Hourly
- Estimated price
- $1–5
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
Bus from Washington St opp Algonquin St to Ruggles
- Ave. Duration
- 29 min
- Frequency
- Every 15 minutes
- Estimated price
- $1–5
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
Bus from Wellington to Laraway Rd @ Winchester Ctr
- Ave. Duration
- 19 min
- Frequency
- Hourly
- Estimated price
- $1–5
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
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