Trip from Plymouth, MA to Winthrop, MA

Last recalculated Apr 16, 2026

Drive Time

1h 3m

Distance

44.9 mi

72 km

Drive Score

7/10

Good drive

Same Day?

Yes, doable

Fuel Cost

one way

EV Charging

Unknown

Best Time to Leave

Save up to 15 min

4 AM

0h 59m ★

6 AM

1h 4m

8 AM

1h 14m

10 AM

1h 7m

12 PM

1h 6m

3 PM

1h 8m

5 PM

1h 14m

8 PM

1h 1m

Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.

Best Time Drive vs Fly

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Plymouth, MA

Wikimedia Commons

Winthrop, MA

Phil Evenden

Trip Overview

The drive from Plymouth, MA to Winthrop, MA covers 44.9 miles and takes about 1h 3m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.

The route leans on Pilgrims Highway, MA 3, Ted Williams Tunnel for much of the mileage, and the overall profile is turn-heavy local drive. The longest uninterrupted segment is about 27.5 miles on Pilgrims Highway. At current regular gas prices, budget about $7.19 one way before food or hotel costs.

Who Is This Route For?

Weekend Trip

Doable as a same-day drive at 1h 3m. Total distance: 44.9 miles.

Family Friendly

Moderate complexity with 0 natural rest stops along the way.

Solo Traveler

1h 3m drive, comfortable solo distance.

EV Driver

0 DC fast chargers along the route. Coverage: unknown.

Scenic Drive

Turn-heavy local drive route profile with national parks nearby.

Drive Character

Expect a 1h 3m drive with frequent turns across 44.9 miles of local and secondary roads.

This route has more turning and local-road decision points than a simple highway run.

There are about 22 navigation steps in the underlying route data, so the final approach matters more than the middle miles.

Pilgrims Highway is the longest continuous segment at about 27.5 miles.

How Hard Is This Drive?

Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.9 miles in near US 44.

Driving Effort 7/10

Demanding - plan breaks and stay ahead of the key maneuvers

Balances navigation complexity with total wheel time.

This drive requires moderate attention. Across 44.9 miles you will encounter 13 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.

Where does it get tricky?

The main spots that need attention: at 0.9 miles (US 44): Multiple destination signs - pick the right one; at 1.2 miles (US 44; MA 3 / Pilgrims Highway): Merge point - match speed before joining. Lane positioning matters here; at 36.9 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.

Critical Maneuvers

5 of 13 key points

These are the spots where you need to pay the most attention. Preview them before you drive.

0.9 mi into trip | ~2m in | US 44

Take the ramp onto US 44 toward MA 3 North: Kingston, Boston

Multiple destination signs - pick the right one

Toward MA 3 North: Kingston, Boston

1.2 mi into trip | ~3m in | US 44; MA 3 / Pilgrims Highway

Merge onto US 44; MA 3 / Pilgrims Highway

Merge point - match speed before joining. Lane positioning matters here

Use the straight / slight right lanes.

36.9 mi into trip | ~48m in

Take the exit toward Massachusetts Avenue, Roxbury, Frontage Road

Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one

Use the straight / slight right lanes. Exit 15B Toward Massachusetts Avenue, Roxbury, Frontage...

38.5 mi into trip | ~52m in

Keep slight left at fork toward I 90 East

Highway fork - watch signs carefully. Lane positioning matters here

Use the slight left lane. Toward I 90 East

43.2 mi into trip | ~1h in | Saratoga Street

Enter roundabout onto Saratoga Street

Roundabout - know your exit number before entering

Towns Mentioned on Route Signs

Based on OSRM destination-sign hints, not a full list of every settlement the road passes.

On the drive from Plymouth, MA to Winthrop, MA, road signs begin pointing toward Roxbury along the way.

Roxbury

36.9 mi in | ~48m

Main Roads

Road	Distance	Duration
Pilgrims Highway	27.5 mi	34m
MA 3	8.2 mi	11m
Ted Williams Tunnel	1.6 mi	2m
Massachusetts Turnpike	1.5 mi	2m
Saratoga Street	0.8 mi	1m
McClellan Highway	0.7 mi	1m
Samoset Street	0.7 mi	1m
Frontage Road Northbound	0.6 mi	1m

Longest stretch: Pilgrims Highway — 27.5 mi, about 34m

Turn-by-Turn Driving Directions

Step-by-step road directions between Plymouth, MA and Winthrop, MA.

Start on MA 3A

0.2 mi · 42 sec · Court Street

Turn left onto US 44

0.7 mi · 1 min · Samoset Street

Take the ramp onto US 44

0.3 mi · 39 sec · US 44

Toward MA 3 North: Kingston, Boston

Merge onto US 44; MA 3

27 mi · 34 min · Pilgrims Highway

Use the straight / slight right lanes.

Continue on MA 3

8.2 mi · 11 min · MA 3

Exit 43B Toward I 93 North: Boston Use the straight / slight right lanes.

Take the exit

0.1 mi · 14 sec

Exit 15B Toward Massachusetts Avenue, Roxbury, Frontage Road Use the straight / slight right lanes.

Turn straight onto Frontage Road Northbound

0.3 mi · 29 sec · Frontage Road Northbound

Use the left / straight lanes.

Continue on Frontage Road Northbound

0.3 mi · 36 sec · Frontage Road Northbound

Take the ramp

0.9 mi · 1 min

Toward I 90 East

Keep slight left at fork

0.3 mi · 34 sec

Toward I 90 East Use the slight left lane.

Merge onto I 90

0.4 mi · 39 sec · Massachusetts Turnpike

Continue on I 90

1.6 mi · 2 min · Ted Williams Tunnel

Continue on I 90

1.1 mi · 1 min · Massachusetts Turnpike

Use the straight / slight right lanes.

Merge onto MA 1A

0.3 mi · 34 sec · East Boston Expressway

Continue on MA 1A

0.7 mi · 1 min · McClellan Highway

Turn right onto Boardman Street

0.4 mi · 47 sec · Boardman Street

Enter roundabout onto Saratoga Street

86 ft · 1 sec · Saratoga Street

Continue on Saratoga Street

0.7 mi · 1 min · Saratoga Street

Continue on MA 145

0.4 mi · 52 sec · Main Street

Turn right onto Hermon Street

0.4 mi · 53 sec · Hermon Street

Continue on Winthrop Street

0.2 mi · 16 sec · Winthrop Street

Arrive at destination

Winthrop Street

Where to Stop

Rest stops, refuel points, and overnight suggestions along this route.

Halfway Point

Midpoint

About 22.5 mi from Plymouth, MA · 29m into the drive

city in Norfolk County, Massachusetts, United States

Mid-route town

Meal stop

Quincy, MA

22 mi into the route

Best for: Lunch, fuel, and a longer reset

This sits close to the middle of the route, so it works well for the longest stop of the day.

Pacing Suggestions

Norwell, MA

Fuel and coffee

A short stop after about 10 miles helps settle the day before fatigue starts building.

Quincy, MA

Meal break

The midpoint is around 22.5 miles from Plymouth, MA, which is a good place for a longer meal and fuel stop.

Arriving in Winthrop, MA

The final approach into Winthrop, MA usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.

These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.

Fuel & Cost

Regular Gas

$7.19 one way

$14.37 round trip

$4.07/gal 25.4 MPG avg 16 kg CO₂

Fuel Type	$/gal	One Way	Round Trip
midgrade	$4.43	$7.84	$15.67
premium	$4.82	$8.53	$17.05
diesel	$5.61	$9.91	$19.83

Estimated Tolls: $0.08

Massachusetts Turnpike (1.5 mi) $0.08

Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.

Drive Cost (one way)

Fuel

Tolls

Total

Estimated CO2 emission: 15.7 kg one way. Prices: EIA weekly data, 2026-04-13.

Driving Electric?

About $5 in charging · 0 stops · 69% less CO₂

Vehicle Type	kWh	DC Fast	Home Charge
Average EV	13.5	$4.71	$2.16
Efficient EV	11.2	$3.93	$1.80
EV Truck/SUV	18	$6.29	$2.87

Gas CO2

16 kg

EV CO2

5 kg (69% less)

This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.

DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.

Travel Intel

Current conditions at both ends of the drive.

Forecast as of Apr 15, 2026

Origin

Plymouth, MA

Afternoon in Plymouth on Thursday

Local time

3:12 PM

EDT

Current temp

41°F

Unavailable

Live forecast

Destination

Winthrop, MA

Afternoon in Winthrop on Thursday

Local time

3:12 PM

EDT

Current temp

63°F

Unavailable

Live forecast

Time zone

Same local time

Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.

Temperature spread

22 degrees warmer at arrival

A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.

Road read

1h 3m on the road

Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.

Weather data from the National Weather Service. Conditions may change; check closer to your travel date.

Frequently Asked Questions

The drive from Plymouth, MA to Winthrop, MA covers 44.9 miles and takes about 1h 3m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.

The main roads are Pilgrims Highway, MA 3, Ted Williams Tunnel. Expect a mix of highway and local road driving.

This is a comfortable same-day trip.

The midpoint is about 22.5 miles from Plymouth, MA. Look for rest areas, gas stations, or food options near the halfway mark.

At current regular gas prices, expect to spend about $7.19 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.

Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.

On the drive from Plymouth, MA to Winthrop, MA, road signs begin pointing toward Roxbury along the way.

Yes. Nearby national parks include Adams National Historical Park, Boston National Historical Park and Boston Harbor Islands National Recreation Area. There are 6 parks within detour distance of this route.

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