Traveling from Oak Bluffs to Somerville covers 87.5 miles and typically takes about 2 hours and 41 minutes. Because this route involves a ferry crossing from Martha's Vineyard followed by a drive north through Massachusetts, it works perfectly as a straightforward one-day trip. Budgeting approximately $14 for fuel will cover your transit from the island to the greater Boston area. You will transition from coastal island roads onto major arteries like the Pilgrims Highway and MA 3. It is a manageable journey that connects the unique atmosphere of the Vineyard to the urban density of Somerville, making it an efficient way to traverse the Northeast corridor.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Break Rhythm
1 planned break
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
43.8 miles from Oak Bluffs, MA
A natural place for your longest stop of the day
, about 1h 40m into the drive
.
Main Roads
Road
Distance
Duration
Pilgrims Highway
42.3 mi
53m
Woods Hole - Oak Bluffs Ferry
8.5 mi
44m
MA 3
8.4 mi
11m
West Falmouth Highway
8.3 mi
11m
General MacArthur Boulevard
4.1 mi
6m
Sandwich Road Connector
3.5 mi
6m
Woods Hole Road
3.3 mi
7m
John F. Fitzgerald Expressway
3.2 mi
5m
Longest stretch:
Pilgrims Highway
— 42.3 mi, about 53m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oak Bluffs, MA and Somerville, MA.
1
Start on Butler Avenue
172 ft·25 sec·Butler Avenue
2
Turn left onto Jordan Crossing
254 ft·31 sec·Jordan Crossing
3
At end of road, turn right onto Siloam Avenue
334 ft·14 sec·Siloam Avenue
4
Continue on Siloam Avenue
498 ft·25 sec·Siloam Avenue
5
At end of road, turn right onto Lake Avenue
0.3 mi·45 sec·Lake Avenue
6
Turn sharp left onto Sea View Avenue
441 ft·11 sec·Sea View Avenue
7
Turn right onto Oak Bluffs Avenue
0.1 mi·34 sec·Oak Bluffs Avenue
8
Turn slight left onto Woods Hole - Oak Bluffs Ferry
8.5 mi·44 min·Woods Hole - Oak Bluffs Ferry
9
Continue
203 ft·18 sec
10
At end of road, turn left onto Railroad Avenue
416 ft·21 sec·Railroad Avenue
11
Merge onto Woods Hole Road
3.3 mi·7 min·Woods Hole Road
12
Continue on Locust Street
0.4 mi·1 min·Locust Street
13
At end of road, turn left onto MA 28
0.1 mi·9 sec·North Main Street
14
Continue on MA 28
1.0 mi·2 min·Palmer Avenue
15
Continue on MA 28
8.3 mi·11 min·West Falmouth Highway
16
Enter roundabout onto MA 28
0.1 mi·17 sec·General MacArthur Boulevard
17
Continue on MA 28
4.0 mi·5 min·General MacArthur Boulevard
18
Enter roundabout onto Sandwich Road Connector
171 ft·5 sec·Sandwich Road Connector
19
Continue on Sandwich Road Connector
3.5 mi·6 min·Sandwich Road Connector
Use the straight lane.
20
Turn right onto Adams Street
0.2 mi·26 sec·Adams Street
21
Turn right onto MA 6A
239 ft·5 sec·Cranberry Highway
22
Take the ramp onto MA 6A
0.2 mi·21 sec·MA 6A
23
Merge onto US 6
0.4 mi·47 sec·Sagamore Bridge
24
Continue on US 6
0.3 mi·20 sec·Pilgrim Highway
25
Continue on MA 3
42 mi·53 min·Pilgrims Highway
Use the straight / slight right lanes.
26
Continue on MA 3
8.4 mi·11 min·MA 3
Exit 43BToward I 93 North: BostonUse the straight / slight right lanes.
27
Continue on I 93; US 1; MA 3
3.2 mi·5 min·John F. Fitzgerald Expressway
Use the straight / slight right lanes.
28
Keep slight right at fork onto I 93
0.6 mi·47 sec·I 93
Toward I 93 North: Concord NHUse the straight / slight left lanes.
29
Take the exit
0.4 mi·1 min
Exit 20Toward Sullivan Square, SomervilleUse the straight / slight right lanes.
30
Turn left onto Cambridge Street
0.2 mi·45 sec·Cambridge Street
Use the left / right lanes.
31
Continue on Washington Street
0.5 mi·1 min·Washington Street
32
Turn right onto McGrath Highway
0.2 mi·25 sec·McGrath Highway
Use the right lane.
33
Turn left onto Medford Street
332 ft·12 sec·Medford Street
Use the left lane.
34
Keep slight left at fork onto Highland Avenue
0.4 mi·1 min·Highland Avenue
35
Turn right
163 ft·12 sec
36
Arrive at destination
Trip Plan
Since this 2-hour and 41-minute drive is relatively short, you have the flexibility to schedule your departure around ferry timetables rather than traffic fatigue. Plan for at least one stop to stretch your legs after the ferry crossing, as the transition from boat to car can be jarring. Keep a close eye on your fuel gauge before leaving Oak Bluffs to avoid higher prices once you hit the mainland. Given the turn-heavy nature of the local roads, ensure your vehicle is ready for frequent gear shifts and stops. Prioritizing your ferry booking is the most important step for this trip, as it dictates your entire arrival time in Somerville.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 43.8 miles from Oak Bluffs, MA, or about 1h 40m into the drive.
The longest continuous stretch on this route runs about 42.3 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 19 miles or 1h 5m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 43.8 miles or 1h 40m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 2h 19m
Traffic, exits, and arrival timing usually matter more near Somerville, MA than in the middle of the route.
Before You Leave
+
Open the route before leaving Oak Bluffs, MA so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Oak Bluffs, MA
This is one driving day of about 87.5 miles and 2h 41m.
Your first comfortable stop window is around 19 miles from Oak Bluffs, MA.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on Pilgrims Highway for about 42.3 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 23
5 decision points cluster between mile 0.1 and 86.1 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0.1 mi into trip|~0m in|Siloam Avenue
At end of road, turn right onto Siloam Avenue
Navigation decision point
6
0.5 mi into trip|~2m in|Sea View Avenue
Turn sharp left onto Sea View Avenue
Sharp turn - reduce speed on approach
7
85.1 mi into trip|~2h 34m in|I 93
Keep slight right at fork onto I 93 toward I 93 North: Concord NH
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight left lanes.
Toward I 93 North: Concord NH
8
85.7 mi into trip|~2h 35m in
Take the exit toward Sullivan Square, Somerville
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 20
Toward Sullivan Square, Somerville
6
86.1 mi into trip|~2h 36m in|Cambridge Street
Turn left onto Cambridge Street
Lane positioning matters here
Use the left / right lanes.
Fuel & Cost
Regular Gas
$14.00 one way
$28.01 round trip
$4.07/gal25.4 MPG avg31 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.43
$15.27
$30.54
premium
$4.82
$16.61
$33.23
diesel
$5.61
$19.32
$38.64
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$14
Meals
$25–$50
Total
$39–$64
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 30.6 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $9 in charging
· 0 stops
· 68% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
26.3
0
$9.19
$4.20
Efficient EV
21.9
0
$7.66
$3.50
EV Truck/SUV
35
0
$12.25
$5.60
Gas CO2
31 kg
EV CO2
10 kg (68% 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 17, 2026
Origin
Oak Bluffs, MA
Night
in Oak Bluffs on Saturday
Local time
10:48 PM
EDT
Current temp
--
Unavailable
Destination
Somerville, MA
Night
in Somerville on Saturday
Local time
10:48 PM
EDT
Current temp
63°F
Patchy Fog then Chance Light Rain
NE 5 to 8 mph32% chanceLive forecast
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Road read
2h 41m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Boston National Historical Park
National Historical Park
Discover how one city could be the Cradle of Liberty, site of the first major battle of American Revolution, and home to many who espoused that freedom can be extended to all.
0 mi from route
~1 min detour
Free
near mile 84.5
Park Closure: Dorchester Heights Temporary Public Access Restrictions
From the sweet little farm at the foot of Penn’s Hill to the gentleman’s country estate at Peace field, Adams National Historical Park is the story of “heroes, statesmen, philosophers…and learned wome...
. . . where you can walk a Civil War-era fort, view historic lighthouses, explore tide pools, hike lush trails, camp under the stars, or relax while fishing, picnicking, or swimming—all within reach o...
5 mi from route
~14 min detour
Free
near mile 78.5
At Minute Man National Historical Park the opening battle of the Revolution is brought to life as visitors explore the battlefields and structures associated with April 19, 1775, and witness the Ameri...
12 mi from route
~29 min detour
Free
near mile 87.5
Originally established in 1938 as the first National Historic Site in the United States, Salem Maritime National Historical Park consists of nine acres of land and twelve historic structures along the...
14 mi from route
~35 min detour
Free
near mile 84.5
"The town itself is perhaps the dearest place to live in, in all New England..nowhere in all America will you find more patrician-like houses, parks and gardens more opulent, than in New Bedford…all t...
15 mi from route
~38 min detour
Free
near mile 9.1
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a turn-heavy local drive that demands your full attention as you navigate off the island and onto the mainland. Only 14% of this 87.5-mile journey is spent on highways, meaning you will spend the majority of your time on smaller, winding roads. Your longest uninterrupted stretch occurs once you reach the Pilgrims Highway, which spans 42.3 miles of the trip. The transition from coastal island navigation to mainland highway driving creates a distinct change in pace behind the wheel. Prepare for a mix of technical turns in the early stages followed by a more consistent flow once you merge onto the primary state routes.
Only 14% highway — the rest is turn-by-turn surface driving.
36 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 42.3 mi on Pilgrims Highway.
How Hard Is This Drive?
9/10
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 0.1 miles in near Siloam Avenue.
Driving Effort9/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 23 significant decision points across 87.5 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 0.1 miles (Siloam Avenue): Navigation decision point; at 0.5 miles (Sea View Avenue): Sharp turn - reduce speed on approach; at 85.1 miles (I 93): Highway fork - watch signs carefully. Lane positioning matters here.
Older Bostonians might still derisively call it "Slummerville", but today that tired old moniker couldn't be further from the truth. Packed with upwardly mobile professionals and longtime residents, Somerville is often voted an "All-America City" and the best-run city in Massachusetts. It would seem civically engaged folks can achieve uncommon results; and Somerville fosters an environment of cooperation like no other. Its 81,000 residents (2020) are quick to enjoy the fruits of their artistry, and you'll find top notch options for dinner, drinks, and dancing all in abundance within Somerville's borders. Lurking just to the south, big brothers Boston and Cambridge provide options and opportunities for many of Somerville's creative class residents.
Doable as a same-day drive at 2h 41m. Total distance: 87.5 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
2h 41m drive, comfortable solo distance.
Scenic Drive
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 42.3 miles on Pilgrims Highway. The full list of main roads is in the Roads section above.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Somerville, MA before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 0.1 miles (Siloam Avenue): Navigation decision point; at 0.5 miles (Sea View Avenue): Sharp turn - reduce speed on approach; at 85.1 miles (I 93): Highway fork - watch signs carefully. Lane positioning matters here.
Yes — Boston National Historical Park, Adams National Historical Park and Boston Harbor Islands National Recreation Area (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at Somerville, MA before heading back.
