How far is Cheshire, MA from Boston, MA?
The driving distance from Cheshire, MA to Boston, MA is about 147.5 miles (237.3 km), with a travel time of about 02h 36m by car.
- The straight-line flight distance is about 108.1 miles (174 km).
- For a round trip, plan for roughly 05h 13m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 02h 36m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
City in Hampden County, Massachusetts, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Rain then Rain Showers Likely
Light Rain Likely
Driving Route Map
The map below follows the saved road route between Cheshire and Boston.
Turn-by-Turn Driving Directions
Step-by-step road directions between Cheshire and Boston.
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1
Start on Church Street
743 ft · 29 sec · Church Street
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2
Turn left onto South Street
1503 ft · 32 sec · South Street
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3
Continue on South State Road
3.4 mi · 6 min · South State Road
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4
Continue on Cheshire Road
3.6 mi · 6 min · Cheshire Road
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5
Continue on Merrill Road
1.5 km · 3 min · Merrill Road
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6
Turn left onto Junction Road
133 m · 12 sec · Junction Road
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7
Continue on Junction Road
55 m · 5 sec · Junction Road
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8
Turn straight onto East Street
1.1 km · 2 min · East Street
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9
Turn left onto Newell Street
2048 ft · 59 sec · Newell Street
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10
Turn left onto Dorchester Avenue
2158 ft · 1 min · Dorchester Avenue
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11
At the end of the road, turn right onto Elm Street
982 ft · 29 sec · Elm Street
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12
Turn left onto Holmes Road
3.5 mi · 8 min · Holmes Road
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13
At the end of the road, turn left onto Pittsfield Road
2 mi · 4 min · Pittsfield Road
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14
Continue on Veterans Memorial Highway
2.3 mi · 3 min · Veterans Memorial Highway
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15
Continue on Lee Road
1.2 mi · 2 min · Lee Road
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16
Continue on Laurel Street
1.2 mi · 2 min · Laurel Street
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17
Continue on West Center Street
959 ft · 13 sec · West Center Street
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18
At the end of the road, turn right onto Main Street
2289 ft · 1 min · Main Street
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19
At the end of the road, turn left onto Park Street
751 ft · 27 sec · Park Street
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20
Continue on Housatonic Street
2865 ft · 1 min · Housatonic Street
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21
Take the exit slight right
1734 ft · 43 sec
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22
Keep slight right
2179 ft · 53 sec
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23
Merge slight left onto Massachusetts Turnpike
123.2 mi · 2 hr 25 min · Massachusetts Turnpike
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24
Take the exit slight left toward I 93: South Station, Concord New Hampshire, Quincy
156 m · 13 sec
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25
Keep slight right to continue on South Station
1718 ft · 47 sec
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26
Turn left onto Kneeland Street
525 ft · 22 sec · Kneeland Street
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27
Turn right onto Lincoln Street
1345 ft · 51 sec · Lincoln Street
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28
At the end of the road, turn left onto Summer Street
25 m · 6 sec · Summer Street
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29
Turn right onto Devonshire Street
687 ft · 32 sec · Devonshire Street
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30
Turn left onto Franklin Street
53 m · 8 sec · Franklin Street
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31
Turn right onto Arch Street
141 m · 20 sec · Arch Street
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32
Turn left onto Milk Street
84 m · 9 sec · Milk Street
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33
Continue on Washington Street
737 ft · 33 sec · Washington Street
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34
At the end of the road, turn left onto Court Street
144 m · 20 sec · Court Street
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35
Turn left onto Tremont Street
102 m · 12 sec · Tremont Street
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36
Arrive at your destination
0 m · 1 sec · Tremont Street
Car Route Details
A richer read on the saved driving route between Cheshire and Boston.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Massachusetts Turnpike
Merge slight left onto Massachusetts Turnpike
123 mi · 02h 25m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Rain then Rain Showers Likely leaving Cheshire and Light Rain Likely near Boston.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Cheshire to Boston?
The road trip is about 147.5 miles (237.3 km) and usually takes 02h 36m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Palmer is a useful midpoint, sitting about 73.4 miles from Cheshire and 74.1 miles from Boston.
How much longer is the road route than the straight-line distance?
The direct path is about 108.1 miles (174 km), while the road route adds roughly 39.4 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 1:16 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $20.23 one way or $40.46 round trip. Estimated CO2 is about 46.2 kg one way.
What should you check before leaving?
Before you leave, expect Rain then Rain Showers Likely around Cheshire and Light Rain Likely near Boston.
Stop Ideas Near Palmer
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Palmer.
Springfield Union Station
Amherst, Massachusetts
Union Station
Windsor Locks
Flight Path Map
This map shows the direct air route between Cheshire and Boston. Straight-line distance: 108.12 mi (174 km).
#1 Cheshire
Town in Massachusetts
| Population | 3,105 |
| Coordinates | 42.5620300, -73.1628800 |
| Altitude | 301 |
| Country | United States |
#2 Boston
The twenty-first most populous city in the United States and the center of the Boston metropolitan area.
| Population | 691,531 |
| Coordinates | 42.3584300, -71.0597700 |
| Altitude | 14 |
| Country | United States |
End: Tremont Street (-71.060061, 42.358547)
Estimated Travel Time
Distance: 237 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 04h 54m |
| 40 mph (64.37 km/h) | 03h 41m |
| 50 mph (80.47 km/h) | 02h 56m |
| 60 mph (96.56 km/h) | 02h 27m |
| 70 mph (112.65 km/h) | 02h 06m |
| 80 mph (129 km/h) | 01h 50m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.89 | $20.23 | $40.46 |
| Mid-grade | $4.40 | $22.86 | $45.73 |
| Premium | $4.80 | $24.95 | $49.91 |
| Diesel | $4.49 | $23.34 | $46.68 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Massachusetts · May 25, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.