How far is Boston, MA from Winchendon, MA?
The driving distance from Boston, MA to Winchendon, MA is about 64.9 miles (104.4 km), with a travel time of about 01h 36m by car.
- The straight-line flight distance is about 55 miles (88.5 km).
- For a round trip, plan for roughly 03h 12m 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 01h 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.
Town in Worcester County, Massachusetts
Route Weather Snapshot
Check the forecast at both ends before you head out.
Partly Sunny then Chance Rain Showers
Partly Sunny then Chance Showers And Thunderstorms
Driving Route Map
The map below follows the saved road route between Boston and Winchendon.
Turn-by-Turn Driving Directions
Step-by-step road directions between Boston and Winchendon.
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1
Start on Tremont Street
70 m · 11 sec · Tremont Street
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2
Turn right onto Beacon Street
92 m · 11 sec · Beacon Street
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3
Turn right onto Somerset Street
104 m · 13 sec · Somerset Street
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4
Turn left onto Ashburton Place
64 m · 7 sec · Ashburton Place
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5
Keep slight right to continue on Ashburton Place
77 m · 9 sec · Ashburton Place
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6
Turn straight onto Bowdoin Street
574 ft · 24 sec · Bowdoin Street
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7
Turn right onto Cambridge Street
134 m · 22 sec · Cambridge Street
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8
Turn left onto Sudbury Street
1490 ft · 1 min · Sudbury Street
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9
Take the ramp left toward I 93 North: Concord NH
1.1 mi · 2 min
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10
Merge slight left
1.3 mi · 2 min
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11
Take the exit slight right toward MA 28, MA 38: Somerville, Medford
780 ft · 20 sec
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12
Keep slight left to continue on MA 28 South, MA 38 North: Somerville, Medford
668 ft · 18 sec
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13
Turn straight onto Mystic Avenue
1.2 mi · 2 min · Mystic Avenue
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14
Turn left onto Harvard Street
1.1 km · 1 min · Harvard Street
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15
Continue on Warner Street
927 ft · 20 sec · Warner Street
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16
Enter the roundabout and take exit 2 toward Powder House Square
39 m · 3 sec · Powder House Boulevard
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17
Exit the rotary onto Powder House Boulevard
1.5 km · 2 min · Powder House Boulevard
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18
At the end of the road, turn left onto Alewife Brook Parkway
1.6 km · 3 min · Alewife Brook Parkway
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19
Turn right onto Concord Turnpike
4.1 mi · 6 min · Concord Turnpike
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20
Continue on Concord Highway
2.9 mi · 4 min · Concord Highway
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21
Continue on Cambridge Turnpike
3.3 mi · 5 min · Cambridge Turnpike
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22
Continue on Concord Turnpike
3.9 mi · 6 min · Concord Turnpike
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23
Continue on Elm Street
1635 ft · 35 sec · Elm Street
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24
Enter the roundabout and take exit 3 toward Concord Rotary
124 m · 5 sec · Union Turnpike
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25
Exit the rotary onto Union Turnpike
3035 ft · 39 sec · Union Turnpike
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26
Continue on Massachusetts Avenue
6.2 mi · 9 min · Massachusetts Avenue
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27
Continue on George W Stanton Highway
1406 ft · 22 sec · George W Stanton Highway
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28
Continue on Captain Isaac Davis Highway
11.2 mi · 15 min · Captain Isaac Davis Highway
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29
Keep slight left to continue on Concord Turnpike
12.2 mi · 17 min · Concord Turnpike
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30
Take the exit slight right toward MA 140 North: Winchendon
1527 ft · 43 sec
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31
Merge slight left onto West Main Street
6.1 mi · 8 min · West Main Street
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32
Continue on Gardner Road
3.4 mi · 4 min · Gardner Road
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33
Continue on Spring Street
2.3 mi · 3 min · Spring Street
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34
Turn right onto Central Street
2359 ft · 42 sec · Central Street
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35
Turn right
40 m · 10 sec
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36
Keep slight right
7 m · 2 sec
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37
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Boston and Winchendon.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Concord Turnpike
Keep slight left to continue on Concord Turnpike
12.2 mi · 00h 17m
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.
Partly Sunny then Chance Rain Showers leaving Boston and Partly Sunny then Chance Showers And Thunderstorms near Winchendon.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Boston to Winchendon?
The road trip is about 64.9 miles (104.4 km) and usually takes 01h 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?
Harvard is a useful midpoint, sitting about 32.4 miles from Boston and 32.5 miles from Winchendon.
How much longer is the road route than the straight-line distance?
The direct path is about 55 miles (88.5 km), while the road route adds roughly 9.9 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 3:18 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $8.91 one way or $17.82 round trip. Estimated CO2 is about 20.4 kg one way.
What should you check before leaving?
Before you leave, expect Partly Sunny then Chance Rain Showers around Boston and Partly Sunny then Chance Showers And Thunderstorms near Winchendon.
Stop Ideas Near Harvard
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
City Hall - Internet Backbone Point
Leominster City Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Harvard.
Framingham station
Union Station
Nashua, NH
Anderson Regional Transportation Center
Flight Path Map
This map shows the direct air route between Boston and Winchendon. Straight-line distance: 55 mi (88.51 km).
#1 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 |
#2 Winchendon
Town in Massachusetts
| Population | 10,835 |
| Coordinates | 42.6862000, -72.0439700 |
| Altitude | 304 |
| Country | United States |
End: Winchendon (-72.04397, 42.6862)
Estimated Travel Time
Distance: 104 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 09m |
| 40 mph (64.37 km/h) | 01h 37m |
| 50 mph (80.47 km/h) | 01h 17m |
| 60 mph (96.56 km/h) | 01h 04m |
| 70 mph (112.65 km/h) | 00h 55m |
| 80 mph (129 km/h) | 00h 48m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.89 | $8.91 | $17.82 |
| Mid-grade | $4.40 | $10.07 | $20.14 |
| Premium | $4.80 | $10.99 | $21.98 |
| Diesel | $4.49 | $10.28 | $20.56 |
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 · Apr 15, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.