How far is Simsbury, CT from Bridgeport, CT?
The driving distance from Simsbury, CT to Bridgeport, CT is about 65.7 miles (105.7 km), with a travel time of about 01h 16m by car.
- The straight-line flight distance is about 52.1 miles (83.9 km).
- For a round trip, plan for roughly 02h 33m 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 16m.
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 Connecticut
Route Weather Snapshot
Check the forecast at both ends before you head out.
Driving Route Map
The map below follows the saved road route between Simsbury and Bridgeport.
Turn-by-Turn Driving Directions
Step-by-step road directions between Simsbury and Bridgeport.
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1
Start on Hopmeadow Street
4.2 mi · 9 min · Hopmeadow Street
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2
Continue on Simsbury Road
1.3 km · 2 min · Simsbury Road
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3
Turn left onto West Main Street
1.2 km · 2 min · West Main Street
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4
Turn right onto Waterville Road
5.6 mi · 11 min · Waterville Road
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5
Continue on Main Street
2.7 mi · 3 min · Main Street
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6
Continue on Farmington Avenue
1.4 mi · 2 min · Farmington Avenue
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7
Continue on East Street
1.7 mi · 2 min · East Street
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8
Continue on Queen Street
2.4 mi · 3 min · Queen Street
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9
Continue on North Main Street
2.4 mi · 3 min · North Main Street
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10
Continue on South Main Street
1.2 mi · 1 min · South Main Street
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11
Continue on Norton Street
2138 ft · 28 sec · Norton Street
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12
Turn straight onto Cheshire Road
1069 ft · 16 sec · Cheshire Road
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13
Continue on Highland Avenue
4.4 mi · 5 min · Highland Avenue
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14
Continue on Main Street
3.1 mi · 4 min · Main Street
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15
Continue on Whitney Avenue
5.4 mi · 7 min · Whitney Avenue
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16
Take the ramp slight right
1084 ft · 26 sec
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17
Merge slight left onto Wilbur Cross Parkway
13.8 mi · 18 min · Wilbur Cross Parkway
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18
Continue on Merritt Parkway
3 mi · 4 min · Merritt Parkway
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19
Take the exit slight right toward CT 8, CT 108: Bridgeport, Waterbury
1242 ft · 24 sec
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20
Keep slight left to continue on CT 8 South, CT 108 South: Bridgeport
2228 ft · 48 sec
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21
Keep slight left to continue on CT 8 South: Bridgeport
1.2 km · 2 min
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22
Merge slight left
3.1 mi · 4 min
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23
Take the exit slight right toward Main Street, Washington Avenue
719 ft · 18 sec
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24
Continue on Main Street, Washington Avenue
111 m · 9 sec
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25
Keep slight left to continue on Main Street South, East Washington Avenue
1381 ft · 34 sec
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26
Turn straight onto Main Street
2720 ft · 1 min · Main Street
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27
Turn right onto Fairfield Avenue
1 m · 1 sec · Fairfield Avenue
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28
Arrive at your destination
0 m · 1 sec · Fairfield Avenue
Car Route Details
A richer read on the saved driving route between Simsbury and Bridgeport.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
Wilbur Cross Parkway
Merge slight left onto Wilbur Cross Parkway
13.8 mi · 00h 18m
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.
Forecast cards are syncing for this route.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Simsbury to Bridgeport?
The road trip is about 65.7 miles (105.7 km) and usually takes 01h 16m 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?
Cheshire is a useful midpoint, sitting about 29.6 miles from Simsbury and 36 miles from Bridgeport.
How much longer is the road route than the straight-line distance?
The direct path is about 52.1 miles (83.9 km), while the road route adds roughly 13.6 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 3:56 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $9.15 one way or $18.30 round trip. Estimated CO2 is about 20.6 kg one way.
Stop Ideas Near Cheshire
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 Cheshire.
Wallingford station
Meriden Transit Center
Berlin
Union Station
Flight Path Map
This map shows the direct air route between Simsbury and Bridgeport. Straight-line distance: 52.16 mi (83.94 km).
#1 Simsbury
Town in Hartford County, Connecticut, United States
| Population | 25,437 |
| Coordinates | 41.8759300, -72.8012100 |
| Altitude | 63 |
| Country | United States |
#2 Bridgeport
The second most populous city in Connecticut.
| Population | 143,525 |
| Coordinates | 41.1792300, -73.1894500 |
| Altitude | 1 |
| Country | United States |
End: Main Street (-73.189437, 41.179239)
Estimated Travel Time
Distance: 106 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 11m |
| 40 mph (64.37 km/h) | 01h 38m |
| 50 mph (80.47 km/h) | 01h 18m |
| 60 mph (96.56 km/h) | 01h 05m |
| 70 mph (112.65 km/h) | 00h 56m |
| 80 mph (129 km/h) | 00h 49m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $9.15 | $18.30 |
| Mid-grade | $4.46 | $10.34 | $20.68 |
| Premium | $4.86 | $11.27 | $22.54 |
| Diesel | $6.00 | $13.91 | $27.83 |
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 Connecticut · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.