Trip from Macedon, NY to Smithtown, NY

Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Apr 19, 2026 · Editorial standards

Drive Time

7h 24m

Distance

347.2 mi

559 km

Drive Score

9/10

Great drive

Same Day?

Yes, doable

Fuel Cost

$57

one way

EV Charging

Good

8 stations

Best Time to Leave

Save up to 31 min

4 AM

7h 15m ★

6 AM

7h 25m

8 AM

7h 46m

10 AM

7h 32m

12 PM

7h 30m

3 PM

7h 33m

5 PM

7h 45m

8 PM

7h 19m

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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town in Wayne County, New York, United States of America

Macedon, NY

Wikimedia Commons

town in Suffolk County, New York, United States

Smithtown, NY

Wikimedia Commons

Trip Overview

Embarking from Macedon, NY, to Smithtown, NY, this journey covers 347.2 miles and is estimated to take around 7 hours and 24 minutes. Primarily utilizing I 81, the Keystone Shortway, and I 380, this drive is manageable as a single-day trip, though you might appreciate a break. The estimated fuel cost for this Northeast to Northeast excursion is approximately $57. With two recommended stops, this route offers a practical way to traverse the region, blending highway travel with more varied road conditions.

Trip Pace

Same-day drive is realistic

A same-day return is possible, but it will make for a full day on the road.

Break Rhythm

2 planned breaks

Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.

Midpoint

173.6 miles from Macedon, NY

A natural place for your longest stop of the day , about 3h 46m into the drive .

Main Roads

Road	Distance	Duration
I 81	98.8 mi	1h 57m
Keystone Shortway	80 mi	1h 37m
I 380	23.6 mi	25m
New York State Thruway	19.2 mi	22m
Long Island Expressway	14.2 mi	19m
Northern State Parkway	13.7 mi	18m
East Lake Road	9.9 mi	14m
State Highway 41	9.8 mi	13m

Longest stretch: I 81 — 98.8 mi, about 1h 57m

Turn-by-Turn Driving Directions

Step-by-step road directions between Macedon, NY and Smithtown, NY.

Start on NY 31

0.5 mi · 1 min · Main Street

Continue on NY 31

2.4 mi · 2 min · State Route 31

Continue on NY 31

0.7 mi · 53 sec · West Main Street

Turn right onto NY 21

0.5 mi · 46 sec · Canandaigua Street

Continue on NY 21

1.1 mi · 1 min · Canandaigua Road

Continue on NY 21

4.3 mi · 6 min · State Route 21

Continue on NY 21

0.2 mi · 19 sec · North Main Street

Take the ramp

0.2 mi · 25 sec

Keep slight right at fork

0.4 mi · 50 sec

Toward I 90 East

Merge onto I 90

19 mi · 22 min · New York State Thruway

Take the exit

0.5 mi · 58 sec

Exit 41 Toward NY 414: Waterloo, Clyde Use the slight right lane.

Keep slight right at fork

327 ft · 7 sec

Continue on NY 414

0.3 mi · 35 sec · State Route 414

Turn left onto NY 318

4.1 mi · 7 min · NY 318

Use the left lane.

At end of road, turn left onto US 20; NY 5

1.9 mi · 2 min · Auburn Road

Continue on US 20; NY 5

9.6 mi · 11 min · Clark Street Road

Use the straight lane.

Turn right onto State Street

226 ft · 12 sec · State Street

Turn left onto Dill Street

0.1 mi · 21 sec · Dill Street

Continue on Loop Road

458 ft · 16 sec · Loop Road

Turn left onto Genesee Street

5.5 mi · 9 min · Genesee Street

Continue on US 20

2.2 mi · 4 min · West Genesee Street Road

Turn right onto NY 41

0.5 mi · 45 sec · East Lake Street

Continue on NY 41

9.4 mi · 13 min · East Lake Road

Continue on NY 41

4.8 mi · 7 min · State Route 41

Continue on NY 41

0.5 mi · 49 sec · East Lake Road

Continue on NY 41

9.8 mi · 13 min · State Highway 41

Turn right onto NY 281

1.2 mi · 2 min · North West Street

Take the ramp

0.7 mi · 1 min

Use the left lane.

Keep slight right at fork

0.3 mi · 34 sec

Toward I 81 South: Binghamton

Merge onto I 81

45 mi · 54 min · I 81

Use the straight / slight right lanes.

Keep slight right at fork onto I 81

53 mi · 1 hr 3 min · I 81

Toward I 81 South: Scranton Use the straight lane.

Keep slight right at fork onto US 6

0.8 mi · 1 min · US 6

Exit 187 Toward I 84 East, I 380 South, US 6 East: Carbondale, Mt Pocono Use the slight left / slight right lanes.

Continue on I 84; I 380

3.7 mi · 4 min · I 84; I 380

Toward I 84 East, I 380 South: Mount Pocono, Milford Use the straight lane.

Keep slight right at fork onto I 380

24 mi · 25 min · I 380

Exit 4 Toward I 380 South: Mount Pocono

Keep slight left at fork

1.0 mi · 1 min

Exit 1B Toward I 80 East: Stroudsburg

Merge onto I 80

80 mi · 1 hr 37 min · Keystone Shortway

Use the straight / right lanes.

Keep slight right at fork onto I 80

5.5 mi · 5 min · Christopher Columbus Highway

Toward I 95: George Washington Bridge Lower Level Use the slight right lane.

Keep slight left at fork

0.3 mi · 23 sec

Toward I 95 North: George Washington Bridge, New York City Use the straight / slight right lanes.

Keep slight right at fork

0.4 mi · 38 sec

Exit 70A-B Toward Leonia, Teaneck Use the slight right lane.

Turn right

0.2 mi · 35 sec

Exit 70A Toward Leonia Use the straight / slight right lanes.

Turn straight onto CR 56

454 ft · 9 sec · Degraw Avenue

Continue on CR 56

1.1 mi · 2 min · Fort Lee Road

Use the straight / right lanes.

Continue on CR 56

469 ft · 13 sec · Main Street

Take the ramp

472 ft · 12 sec

Toward George Washington Bridge

Merge onto US 1; US 9; US 46

0.3 mi · 28 sec · Bergen Boulevard

Use the straight / slight right lanes.

Take the exit

312 ft · 4 sec

Toward George Washington Bridge Upper Level

Merge onto I 95 EXPR

0.3 mi · 20 sec · I 95 EXPR

Use the straight / slight right lanes.

Keep slight left at fork onto I 95 EXPR

0.8 mi · 1 min · I 95 EXPR

Continue on I 95; US 1; US 9

0.6 mi · 1 min · George Washington Bridge (upper level)

Use the straight / slight right lanes.

Continue on I 95; US 1

0.7 mi · 1 min · Trans-Manhattan Expressway

Continue on I 95; US 1

4.7 mi · 6 min · Cross Bronx Expressway

Use the straight / slight right lanes.

Keep slight right at fork onto I 295

2.0 mi · 2 min · Cross Bronx Expressway

Exit 6B Toward I 295 South: Throgs Neck Bridge Use the straight / slight left lanes.

Merge onto I 295

0.6 mi · 58 sec · Throgs Neck Expressway

Continue on I 295

2.0 mi · 3 min · Throgs Neck Bridge

Use the straight / slight right lanes.

Continue on I 295

3.2 mi · 3 min · Clearview Expressway

Use the straight / slight right lanes.

Take the exit

0.2 mi · 27 sec

Exit 4E-W Toward I 495: Manhattan, Eastern Long Island Use the straight / slight right lanes.

Keep slight left at fork

0.3 mi · 38 sec

Exit 4E Toward I 495 East: Long Island Expressway, Eastern Long Island

Merge onto I 495

14 mi · 19 min · Long Island Expressway

Use the straight / slight right lanes.

Take the exit

0.4 mi · 52 sec

Exit 42 Toward N East: Hauppauge Use the slight right lane.

Merge onto N

14 mi · 18 min · Northern State Parkway

Use the straight / slight right lanes.

Take the exit

0.2 mi · 25 sec

Exit 45 Toward SM North: Kings Park Use the right lane.

Merge onto SA

499 ft · 6 sec · Sagtikos State Parkway

Continue on SM

1.7 mi · 1 min · Sunken Meadow State Parkway

Take the exit

0.2 mi · 30 sec

Exit SM3E Toward NY 25 East: Jericho Turnpike East, Smithtown Use the slight right lane.

Turn slight right onto NY 25

3.9 mi · 5 min · Jericho Turnpike

Continue on NY 25; NY 25A

0.6 mi · 54 sec · West Main Street

Use the left lane.

Arrive at destination

NY 25; NY 25A

Trip Plan

Given the 7-hour duration, starting your drive from Macedon early in the morning will allow you to reach Smithtown with daylight to spare. Plan for your two stops to break up the drive and stretch your legs, perhaps around the halfway point or when you transition between major highway segments. Keep an eye on your fuel, especially before entering longer stretches where services might be less frequent. The longest continuous drive is 98.8 miles on I 81, so ensure you're fueled up before that segment.

Morning Departure

Start early — leave by 6-7 AM to arrive at a reasonable hour.

Evening Departure

This is a long drive — plan for a morning departure or consider splitting it into two days.

You can normally do this drive in one day.

Plan roughly 2 meaningful breaks for fuel, food, and rest.

The halfway point lands around 173.6 miles from Macedon, NY, or about 3h 46m into the drive.

The longest continuous stretch on this route runs about 98.8 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 76 miles or 1h 47m in

Use this first pause for coffee, a restroom break, and a quick traffic check ahead.

Halfway reset

Around 173.6 miles or 3h 46m in

This is the best place for your longest stop, a real meal, and a full fuel check.

Final approach

Final hour starts around 6h 1m

Traffic, exits, and arrival timing usually matter more near Smithtown, NY than in the middle of the route.

Before You Leave

Open the route before leaving Macedon, NY 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.

Pick one backup stop option before the midpoint in case traffic changes your pacing.

Day 1

Settle into the route from Macedon, NY

This is one driving day of about 347.2 miles and 7h 24m.

Your first comfortable stop window is around 76 miles from Macedon, NY.

This route can stay practical as a one-day drive if traffic stays reasonable.

Plan about 2 real breaks rather than only quick fuel stops.

The longest stretch is on I 81 for about 98.8 miles.

Where to Stop

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

town in Rockland County, New York, United States

Mid-route town

Meal stop

Ramapo, NY

174 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

Homer, NY

Fuel and coffee

A short stop after about 76 miles helps settle the day before fatigue starts building.

Vestal, NY

Meal break

The midpoint is around 173.6 miles from Macedon, NY, which is a good place for a longer meal and fuel stop.

Before the longest stretch

Fuel check

Top up before I 81 if your tank is already low. That segment runs about 98.8 miles.

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

Nearby Places

Restaurants, cafes, gas stations and more along your route.

Top Restaurant

Bosphorus Restaurant

4.6 ★ ★ ★ ★ ★

Lake Hiawatha, New Jersey

Later in the drive, short detour

1.5 mi from route ~4 min detour $20 to $30 mile 272.8

Hours: 10:30 am–9 pm

+19733359690

Visit website

Triplets Family Restaurant

4.5 ★ ★ ★ ★ ★

Stroudsburg, Pennsylvania

2.6 mi

Top Coffee Stop

Duaa’s Cafe

4.8 ★ ★ ★ ★ ★

New York, New York

Near the end, short detour

1.6 mi from route ~4 min detour $10 to $20 mile 297.6

+19172614093

Lily and Liam

4.4 ★ ★ ★ ★ ☆

Englewood, New Jersey

2.6 mi

Bosphorus Restaurant

4.6 ★ ★ ★ ★ ★

Later in the drive, short detour

1.5 mi from route ~4 min detour $20 to $30 mile 272.8

Lake Hiawatha, New Jersey

Hours: 10:30 am–9 pm

+19733359690

Visit website

Triplets Family Restaurant

4.5 ★ ★ ★ ★ ★

Around the midpoint, short detour

2.6 mi from route ~6 min detour $10 to $20 mile 223.2

Stroudsburg, Pennsylvania

Hours: 5 am–9 pm

+15704216566

Visit website

Park Cafe

4.8 ★ ★ ★ ★ ★

Near the end, ~9 min detour

3.7 mi from route ~9 min detour $1 to $10 mile 297.6

New York, New York

Hours: 8 am–6 pm

+15167490697

Fasil Mediterranean Restaurant

4.5 ★ ★ ★ ★ ★

Later in the drive, ~10 min detour

3.9 mi from route ~10 min detour $20 to $30 mile 272.8

Boonton, New Jersey

Hours: 11 am–10 pm

+19739173334

Visit website

Hapgoods Restaurant & Bar

4.6 ★ ★ ★ ★ ★

Later in the drive, ~10 min detour

4.1 mi from route ~10 min detour $20 to $30 mile 272.8

Mountain Lakes, New Jersey

Hours: 7 am–9 pm

+19732993399

Visit website

Effy's Cafe

4.4 ★ ★ ★ ★ ☆

Near the end, ~10 min detour

4.2 mi from route ~10 min detour $10 to $20 mile 297.6

New York, New York

Hours: 8 am–9 pm

+12122806200

Visit website

Cinar Mediterranean Restaurant

4.6 ★ ★ ★ ★ ★

Later in the drive, ~11 min detour

4.4 mi from route ~11 min detour Moderately mile 272.8

Livingston, New Jersey

Hours: 11:30 am–8:30 pm

+19733151616

Visit website

Paola's

4.5 ★ ★ ★ ★ ★

Near the end, ~12 min detour

4.7 mi from route ~12 min detour $50 to $10 mile 297.6

New York, New York

Hours: 11 am–3 pm

+12127941890

Visit website

Duaa’s Cafe

4.8 ★ ★ ★ ★ ★

Near the end, short detour

1.6 mi from route ~4 min detour $10 to $20 mile 297.6

New York, New York

+19172614093

Lily and Liam

4.4 ★ ★ ★ ★ ☆

Near the end, short detour

2.6 mi from route ~7 min detour mile 297.6

Englewood, New Jersey

Hours: Closed

+12015675111

Visit website

Cafe Amrita

4.1 ★ ★ ★ ★ ☆

Near the end, ~9 min detour

3.6 mi from route ~9 min detour $10 to $20 mile 297.6

New York, New York

Hours: 8 am–11 pm

+12122220683

Visit website

Wonderland Play and Party

4.4 ★ ★ ★ ★ ☆

Near the end, ~12 min detour

4.6 mi from route ~12 min detour mile 297.6

South Hackensack, New Jersey

Hours: 10 am–7 pm

+12014265898

Visit website

Marimba Cafe

4.8 ★ ★ ★ ★ ★

Near the end, ~12 min detour

4.8 mi from route ~12 min detour $10 to $20 mile 297.6

Hackensack, New Jersey

Hours: 7 am–7 pm

+12012563010

Visit website

Flying J EV Charging Station

4.0 ★ ★ ★ ★ ☆

Around the midpoint, right off the route

0.3 mi from route ~1 min detour mile 148.8

New Milford, Pennsylvania

Hours: Open 24 hours

+15704652974

Visit website

EVgo Charging Station

3.6 ★ ★ ★ ★ ☆

Around the midpoint, right off the route

0.3 mi from route ~1 min detour mile 148.8

New Milford, Pennsylvania

Hours: Open 24 hours

+15704652974

Visit website

EVolve NY Charging Station

5.0 ★ ★ ★ ★ ★

Near the start, short detour

1.6 mi from route ~4 min detour mile 24.8

Phelps, New York

Hours: Open 24 hours

+18336322778

Visit website

Electrify America Charging Station

3.7 ★ ★ ★ ★ ☆

Near the start, short detour

1.4 mi from route ~3 min detour mile 24.8

Waterloo, New York

Hours: Open 24 hours

+18336322778

Visit website

Electrify America Charging Station

4.1 ★ ★ ★ ★ ☆

Around the midpoint, short detour

1.9 mi from route ~5 min detour mile 124

Binghamton, New York

Hours: Open 24 hours

+18336322778

Visit website

Electrify America Charging Station

4.6 ★ ★ ★ ★ ★

Around the midpoint, short detour

2.6 mi from route ~6 min detour mile 124

Binghamton, New York

Hours: Open 24 hours

+18336322778

Visit website

IONNA Charging Station

4.2 ★ ★ ★ ★ ☆

Around the midpoint, short detour

2.5 mi from route ~6 min detour mile 173.6

Scranton, Pennsylvania

Hours: Open 24 hours

+18334662474

Visit website

Tesla Supercharger

4.1 ★ ★ ★ ★ ☆

Around the midpoint, short detour

2.9 mi from route ~7 min detour mile 124

4.6 ★ ★ ★ ★ ★

Near the end, right off the route

0.2 mi from route ~1 min detour mile 297.6

Fort Lee, New Jersey

Hours: 10 am–4:45 pm

+12014611776

Visit website

Ross Dock Picnic Area

4.7 ★ ★ ★ ★ ★

Near the end, right off the route

0.6 mi from route ~1 min detour mile 297.6

Fort Lee, New Jersey

Hours: 6 am–7 pm

+12017681360

Visit website

J. Hood Wright Park

4.6 ★ ★ ★ ★ ★

Near the end, short detour

1.1 mi from route ~3 min detour mile 297.6

New York, NY

Hours: 6 am–1 pm

+12126399675

Visit website

Bennett Park

4.5 ★ ★ ★ ★ ★

Near the end, short detour

1.2 mi from route ~3 min detour mile 297.6

New York, NY

Hours: 6 am–1 pm

+12126399675

Visit website

Firemen's Park

4.3 ★ ★ ★ ★ ☆

Near the end, right off the route

0.7 mi from route ~2 min detour mile 297.6

Fort Lee, New Jersey

Hours: Closed

+12015923750

Visit website

Fort Tryon Park

4.7 ★ ★ ★ ★ ★

Near the end, short detour

1.7 mi from route ~4 min detour mile 297.6

New York, New York

Hours: 6 am–1 pm

+12127951388

Visit website

Fort Tryon

4.8 ★ ★ ★ ★ ★

Near the end, short detour

1.6 mi from route ~4 min detour mile 297.6

New York, New York

Hours: 6 am–1 pm

Visit website

Riverbank State Park

4.6 ★ ★ ★ ★ ★

Near the end, short detour

1.9 mi from route ~5 min detour mile 297.6

New York, New York

Hours: 6 am–11 pm

+12126943600

Visit website

Place data sourced from public business listings. Hours and availability may vary.

Heads-up: tricky spots

5 of 41

5 decision points cluster between mile 29.5 and 304.1 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.

29.5 mi into trip | ~37m in

Take the exit toward NY 414: Waterloo, Clyde

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

Use the slight right lane. Exit 41 Toward NY 414: Waterloo, Clyde

179.8 mi into trip | ~3h 53m in | US 6

Keep slight right at fork onto US 6 toward I 84 East, I 380 South, US 6 East: Carbondale, Mt Pocono

Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one

Use the slight left / slight right lanes. Exit 187 Toward I 84 East, I 380 South, US 6 East: Carbo...

294.4 mi into trip | ~6h 9m in

Keep slight left at fork toward I 95 North: George Washington Bridge, New York City

Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one

Use the straight / slight right lanes. Toward I 95 North: George Washington Bridge, Ne...

294.7 mi into trip | ~6h 10m in

Keep slight right at fork toward Leonia, Teaneck

Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one

Use the slight right lane. Exit 70A-B Toward Leonia, Teaneck

304.1 mi into trip | ~6h 24m in | I 295 / Cross Bronx Expressway

Keep slight right at fork onto I 295 / Cross Bronx Expressway toward I 295 South: Throgs Neck Bridge

Highway fork - watch signs carefully. Lane positioning matters here

Use the straight / slight left lanes. Exit 6B Toward I 295 South: Throgs Neck Bridge

Fuel & Cost

Regular Gas

$57.15 one way

$114.30 round trip

$4.18/gal 25.4 MPG avg 122 kg CO₂

Fuel Type	$/gal	One Way	Round Trip
midgrade	$4.52	$61.80	$123.60
premium	$4.92	$67.29	$134.59
diesel	$5.61	$76.66	$153.31

Estimated Tolls: $23.78

George Washington Bridge $16.00

Throgs Neck Bridge $6.55

New York State Thruway (19.2 mi) $0.96

Jericho Turnpike (3.9 mi) $0.27

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

Estimated Trip Cost (one way, 1 person)

Fuel

$57

Tolls

$24

Meals

$25–$50

Total

$106–$131

Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.

Estimated CO2 emission: 121.5 kg one way. Prices: EIA weekly data, 2026-04-13.

Driving Electric?

About $36 in charging · 1 stop · 66% less CO₂

Vehicle Type	kWh	Stops	DC Fast	Home Charge
Average EV	104.2	1	$36.46	$16.67
Efficient EV	86.8	0	$30.38	$13.89
EV Truck/SUV	138.9	1	$48.61	$22.22

Gas CO2

121 kg

EV CO2

41 kg (66% less)

Plan for 1 charging stop. A 30-minute DC fast charge mid-route should be enough to complete the trip comfortably.

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

Macedon, NY

Late night in Macedon on Sunday

Local time

3:44 AM

EDT

Current temp

43°F

Unavailable

Live forecast

Destination

Smithtown, NY

Late night in Smithtown on Sunday

Local time

3:44 AM

EDT

Current temp

48°F

Unavailable

Live forecast

49°F

Ramapo, NY

174 mi in

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.

Temperature spread

5 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

African Burial Ground National Monument

National Monument

The African Burial Ground stands as the oldest and largest known excavated burial site in North America for both free and enslaved Africans. It offers a profound testament to the enduring legacy of Af...

10 mi from route ~25 min detour Free near mile 299.4

View on nps.gov

Park data from the National Park Service API. Alerts update every 2 hours.

What kind of drive is this?

This drive presents a "turn-heavy local drive" profile, with 57% of the journey on highways. While there's a significant uninterrupted stretch of 98.8 miles on I 81, be prepared for a more dynamic experience as you navigate through various road types. The route shifts from open highway to more involved local roads, requiring your attention to navigate the turns and transitions effectively. It's not a monotonous interstate cruise, but rather a route that keeps you engaged behind the wheel.

Only 57% highway — the rest is turn-by-turn surface driving.

67 navigation steps total — most of the decisions cluster near the start and finish.

Longest single stretch: 98.8 mi on I 81.

How Hard Is This Drive?

10/10

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 29.5 miles in.

Driving Effort 10/10

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 41 significant decision points across 347.2 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 29.5 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 179.8 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 294.4 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.

Towns Mentioned on Route Signs

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

Between Macedon, NY and Smithtown, NY, road signs point toward Clyde, Mt Pocono, Milford, New York City, Leonia and Teaneck - among others.

Clyde

29.5 mi in | ~37m

Mt Pocono

179.8 mi in | ~3h 53m | via US 6

Milford

180.6 mi in | ~3h 55m | via I 84; I 380

New York City

294.4 mi in | ~6h 9m

Leonia

294.7 mi in | ~6h 10m

Teaneck

294.7 mi in | ~6h 10m

George Washington Bridge Upper Level

296.9 mi in | ~6h 14m

Eastern Long Island

311.9 mi in | ~6h 34m

N East: Hauppauge

326.4 mi in | ~6h 55m

About the Cities

Starting in Macedon, NY

Full guide →

Founded 1789

Arriving in Smithtown, NY

Full guide →

Smithtown is a town of 117,000 people (2016) in Suffolk County, on Long Island, in New York. Smithtown is comprised of the villages and hamlets of Commack (in part, with the Town of Huntington), Fort Salonga (in part, with the Town of Huntington), Hauppauge (in part, with the Town of Islip), Head of the Harbor, Kings Park, Lake Ronkonkoma (in part with the Town of Brookhaven and Town of Islip), Nesconset, Nissequogue, Smithtown, St. James, & Village of the Branch.

City content from Wikivoyage (CC BY-SA 4.0) and Wikidata (CC0).

Who Is This Route For?

Weekend Trip

Doable as a same-day drive at 7h 24m. Total distance: 347.2 miles.

Family Friendly

Moderate complexity with 2 natural rest stops along the way.

Solo Traveler

7h 24m drive, plan rest stops for pacing.

Scenic Drive

Mostly surface roads route profile with national parks nearby.

Frequently Asked Questions

The longest stretch is about 98.8 miles on I 81. The full list of main roads is in the Roads section above.

Expect about $23.78 in tolls one way, starting with George Washington Bridge. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.

Yes — we found about 30 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.

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 Smithtown, NY 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 2 meaningful breaks. There are 30 rest areas along the route for bathroom stops.

Yes — Hamilton Grange National Memorial, Harriet Tubman National Historical Park and General Grant National Memorial (6 total within detour distance). See the National Parks section for detour distances and tips on detours.

Not recommended in a single day. At 7.4 hours each way, a round trip means 14.8 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Smithtown, NY before the return drive.

How this page is built

Compiled by the US Trip Planner planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, and NPS for national parks. See our methodology for refresh cadence and limitations.

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