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Route guide Route 20 Road Trip

Twenty Route 20 Experiences for the Centennial

The Route 20 designation reaches its centennial in 2026. This page marks that moment by pointing into twenty existing route experiences, from the Pacific endpoint to the Boston finish, rather than treating every road or attraction in the guide as a century old.

Read this as a west-to-east discovery sequence. The numbers are a reading order only, not a ranking or a prescribed travel direction. The centennial belongs to the US Route 20 designation, not to every present-day road, endpoint, alignment, or attraction along the way.

Pacific and western mountain chapters

1 · Oregon

Reach the Pacific endpoint in Newport

Use Newport for a Pacific-endpoint chapter of the current Route 20 story. It is a later endpoint reached through the route's westward growth.

Bend to Newport trip · Oregon guide

2 · Oregon

Cross Santiam Pass from Sisters toward the Willamette Valley

Use this mountain chapter to connect the central Oregon side of Route 20 with the westward run toward the valley and coast.

Santiam Pass segment · Bend to Newport trip

3 · Oregon

Drive Oregon's high desert from Vale to Bend

Take this existing trip when a wide-open Oregon chapter is the right scale for your Route 20 plan.

Oregon guide · Vale

4 · Idaho

Use Boise as the Idaho city reset

Make Boise a larger-city pause within an Idaho sequence that otherwise moves through broad Route 20 country.

Fairfield to Caldwell trip · Idaho guide

5 · Idaho

Cross central Idaho from Arco to Fairfield

Use this interior chapter to follow the existing Arco-to-Fairfield route story without turning it into a separate detour plan.

Arco to Fairfield segment · Idaho guide

6 · Montana and Idaho

Re-enter the Route 20 story west of Yellowstone

Start the west-side chapter at the park edge: the US Route 20 designation does not continue through Yellowstone National Park.

West Yellowstone · Island Park

7 · Wyoming

Approach Yellowstone through Cody and Wapiti Valley

Use the east-side approach for the final Route 20 chapter before the designation stops at the Yellowstone park boundary.

Wapiti · Yellowstone East Entrance

8 · Wyoming

Cross the Bighorn Basin from Thermopolis to Cody

Use this Wyoming trip to connect the Bighorn Basin chapter with the Cody side of the route.

Thermopolis to Greybull segment · Wyoming guide

Plains and heartland chapters

9 · Nebraska

Follow Route 20 across the Nebraska Sandhills

Use the Sandhills segment for a long rural chapter that keeps the route's Nebraska geography in view.

Nebraska guide · Valentine

10 · Iowa and Nebraska

Make the Missouri River handoff at Sioux City

Use Sioux City as the planning handoff between the Iowa and Nebraska sides of the Route 20 story.

South Sioux City · South Sioux City to Randolph segment

11 · Iowa

Link Dubuque, Dyersville, and Waterloo

Follow this existing Iowa trip to connect three named stops into one bounded eastern-Iowa chapter.

Dubuque to Independence segment · Iowa guide

12 · Iowa

Cross western Iowa from Fort Dodge to Sioux City

Use the existing western-Iowa trip when you want a defined corridor between Fort Dodge and Sioux City.

Fort Dodge to Williams segment · Iowa guide

Great Lakes and Midwest chapters

13 · Illinois

Spend a heritage weekend between Galena and Freeport

Use this Illinois trip for a heritage-focused Route 20 chapter anchored by Galena and Freeport.

Galena · Freeport

14 · Illinois

See where modern US 20 crosses historic Route 66

Use Countryside for the physical-crossing story, where modern US 20 meets the historic Route 66 alignment; it remains the authority for that location.

Route 20 and historic Route 66 · Chicago Approach segment

15 · Indiana

Travel from the Indiana Dunes gateway to South Bend

Use this Indiana trip to connect the Dunes gateway with the South Bend side of the corridor.

Gary and Dunes Gateway segment · South Bend

16 · Ohio

Explore Ohio's Western Reserve corridor

Use this existing trip to enter the Western Reserve as one connected Route 20 chapter.

Ohio Western Reserve region · Ohio guide

17 · Pennsylvania

Follow Pennsylvania's Lake Erie corridor

Use this Pennsylvania trip for a bounded Lake Erie-side chapter of Route 20.

Pennsylvania Lake Erie corridor · Pennsylvania guide

New York and New England finish

18 · New York

Move through the Finger Lakes to Auburn

Use this trip to connect a Finger Lakes chapter with the Auburn side of the route.

Canandaigua to Auburn segment · New York guide

19 · Massachusetts

Drive the Berkshires and Jacob's Ladder

Use this Massachusetts trip for a Berkshires and Jacob's Ladder chapter before the eastern finish.

Lee and Jacob's Ladder approach · Massachusetts guide

20 · Massachusetts

Reach the eastern endpoint at Kenmore Square

Use the Boston and Kenmore trip for the established eastern-endpoint chapter of Route 20.

Kenmore · Boston

Plan from the linked authority

Each card is a handoff, not a replacement for the linked place, trip, segment, or state page. Use those pages and current official sources to check details such as access, closures, weather, hours, and legal stopping conditions before you travel.

Keep the route useful after the anniversary

The centennial is one point in Route 20’s long story. These twenty chapters remain useful after 2026 because they lead back to the guide’s established route-planning authority whenever you are ready to choose a real stretch of road.