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Road Trip down U.S. Route 20: America's longest road

12 states and 3,365 miles of transcontinental America.

  • 45
  • 64:50
  • 3,549 mi
  • $491
Take This Trip

Created by Anna Hider - May 17th 2016

Route 66 might be known as America's Mother Road, but U.S. Route 20 is, without question, the Big Daddy. It's America's longest road, stretching from Boston, Massachusetts to Newport, Oregon. That's 12 states and 3,365 miles of transcontinental American awesomeness to explore. Go big and then go home with a mega road trip along this epic route!

1
Photo of Old North Church
4.5

193 Salem St, Boston, MA, US

Old North Church

1

Driving across the whole country, you're bound to pass tons of classic American stops. Start in Boston, where the country basically began, and honor the American Revolution with a visit to the Old North Church.

2
61mi 01h 03m

1 Old Sturbridge Village Rd, Sturbridge, MA, US

Old Sturbridge Village

2
3
36mi 00h 38m

1000 W Columbus Ave, Springfield, MA, US

Plan B Burger Bar

3
4
103mi 01h 41m

32 Washington Ave, Schenectady, NY, US

The Stockade Inn

4
5
61mi 01h 18m

25 Main St, Cooperstown, NY, US

Baseball Hall of Fame

5

Pay tribute to America's favorite pasttime at the Baseball Hall of Fame.

6
59mi 01h 17m

3883 Stone Quarry Rd, Cazenovia, NY, US

Stone Quarry Hill Art Park

6
7
43mi 00h 58m

180 South Street Rd, Auburn, NY, US

Harriet Tubman Home

7

Stop by the former home of American legend Harriet Tubman.

8
45mi 00h 56m
Photo of Sonnenberg Gardens
4.2

151 Charlotte St, Canandaigua, NY, US

Sonnenberg Gardens

8
10

via Pond Rd

24mi 00h 34m

23 E Main St, Le Roy, NY, US

Jell-O Gallery Museum

10
11
56mi 00h 59m
Photo of Buffalo Central Terminal
4.0

495 Paderewski Dr, Buffalo, NY, US

Buffalo Central Terminal

11
12
94mi 01h 40m
12
13
100mi 01h 42m
Photo of Rock and Roll Hall of Fame and Museum
4.5

1100 Rock and Roll Blvd, Cleveland, OH, US

Rock and Roll Hall of Fame and Museum

13

The route also wanders through Cleveland, where you can jam out at the Rock 'n' Roll Hall of Fame.

14
59mi 01h 04m

7000 Kalahari Dr, Sandusky, OH, US

Kalahari Resort

FastBook
$$$$

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14
15
59mi 01h 03m

1902 Front St, Toledo, OH, US

Tony Packo's Cafe

15
16
84mi 01h 29m

1212 West Maumee Street, Angola, IN, US

Timbers Casual Dining & Lounge

16
17
53mi 00h 56m
Photo of Bonneyville Mill
4.6

53413-53999 County Road 131, Middlebury, IN, US

Bonneyville Mill

17
18
73mi 01h 21m

208 Lake Front Dr., Beverly Shores, IN, US

Century of Progress Architectural District

18
19
54mi 01h 04m

233 S Wacker Dr, 103rd Floor, Chicago, IL, US

Willis Tower & Chicago Skydeck

19

Once you reach Chicago, you can get a crazy view of the city from atop the Willis Tower (better known as the Sears Tower).

20
12mi 00h 19m

951 Chicago Ave, Oak Park, IL, US

Frank Lloyd Wright Home & Studio

20

Brush up on your architecture knowledge at Frank Lloyd Wright's house.

Anna Hider

Just a Civil War beard enthusiast, writer at Roadtrippers, and aspiring astronaut reaching for the stars.