Exploring Historic Route 20

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Exploring Historic Route 20 Taking you on an unforgettable adventure along America’s Longest Highway - Boston, MA to Newport, OR
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At 3,365 miles, we aim to raise the profiles of small town, historic sites, mom and pop shop along the original 1926 alignments of US Route 20. The longest highway in the US runs from Boston to Newport, OR

Join us this Sunday, October 18 for a new program on Historic Route 20 and how America's Longest Highway shaped the 250 ...
10/14/2026

Join us this Sunday, October 18 for a new program on Historic Route 20 and how America's Longest Highway shaped the 250 year history of the United States.

All are welcome - Free!

10/11/2026

If you’re traveling Historic US Route 20 through Central New York, there’s one destination that’s worth stopping for: Beak & Skiff Apple Orchards in LaFayette, New York! 🍏

🌳 A Little History: Founded in 1911 by the Beak and Skiff families, this orchard began as a small family apple-growing operation and grew into one of New York’s best-known apple destinations. More than a century later, it remains a family-rooted business celebrating the region’s rich apple-growing heritage.

🍎 A Popular Fall Destination: Every autumn, visitors flock here for fresh-picked apples, c***r, donuts, family-friendly activities, and beautiful views across the rolling orchards. It’s become a favorite fall getaway for families, photographers, and anyone looking to experience the best of New York’s apple country.

📍 Right Along the Route 20 Story: Located at 2708 Lords Hill Road in LaFayette, just south of the US Route 20 corridor, Beak & Skiff makes a wonderful detour for travelers exploring the historic highway across New York State.

🕒 Hours: Operating hours vary by season and activity, especially during the busy fall harvest. Check Beak & Skiff’s official website before visiting for current orchard, store, and attraction hours.

🚗 Whether you’re following Route 20 for its history, its small towns, or its scenic countryside, this is a stop that captures the spirit of a classic American road trip.

Historic highways. Family traditions. Fresh apple c***r. That’s the magic of the open road! 🍎🇺🇸

Did you know that from its origin in 1926 until 1940 - Route 20 began in front of the Massachusetts State House?Its east...
10/09/2026

Did you know that from its origin in 1926 until 1940 - Route 20 began in front of the Massachusetts State House?

Its eastern terminus was at Beacon and Park St and continued down Beacon Street where in turned onto Commonwealth Ave at Kenmore Square.

Where is all begins on the west coast in Newport, Oregon!
10/08/2026

Where is all begins on the west coast in Newport, Oregon!

The historic Lena Water Tower in Lena, Illinois is a true local landmark—122.5 feet of limestone and red brick, built af...
10/04/2026

The historic Lena Water Tower in Lena, Illinois is a true local landmark—122.5 feet of limestone and red brick, built after years of fire troubles and still serving the village today. Listed on the National Register of Historic Places, it’s one of only a few of its kind in the state and a proud symbol of the community.

You’ll spot it easily: just north of US Route 20 (about a mile off the highway) as you travel west from Freeport toward Galena. Next time you’re on the road, take a quick detour and look up—history’s right there!

If you’re traveling US Route 20 between Lusk and Van Tassell, Wyoming, keep an eye out for a reminder that this quiet st...
10/02/2026

If you’re traveling US Route 20 between Lusk and Van Tassell, Wyoming, keep an eye out for a reminder that this quiet stretch of highway was once part of a much bigger story.

Along the road, a historic monument marks the Texas Trail — 1876 to 1897, the route used by thousands of head of cattle driven north from Texas toward the summer ranges of Wyoming and Montana. (Historical Marker Database)

These weren’t short cattle drives. Herds traveled hundreds of miles across the Great Plains, following the grass and water that determined their route. One branch of the trail entered Wyoming near Pine Bluffs, crossed the North Platte, and continued northward through eastern Wyoming toward Montana. (Niobrara County Library)

The cattle helped supply the growing northern cattle industry at a time when the great herds of wild buffalo were rapidly disappearing.

The monument was dedicated in 1940 by Wyoming’s Historical Landmarks Commission. Its artwork includes a cowboy, longhorn cattle, and the brands associated with the outfits that once moved cattle along these trails. (Waymarking)

Today, US Route 20 carries travelers across Wyoming—but here, for a moment, you can imagine a very different kind of traffic: longhorns, cowboys, dust, and a seemingly endless trail stretching from Texas toward Montana.

Just outside Cody, the Route 20 plunges into a dramatic gorge carved by the Shoshone River between Rattlesnake Mountain ...
10/01/2026

Just outside Cody, the Route 20 plunges into a dramatic gorge carved by the Shoshone River between Rattlesnake Mountain (north) and Cedar Mountain (south). Steep canyon walls rise hundreds of feet, the river rushes below, and the road threads through a series of tunnels blasted into the rock—engineering that dates to the early 1900s construction of Buffalo Bill Dam. 

• Gateway to Yellowstone: This is the main east approach to the park’s East Entrance, following the North Fork of the Shoshone River through the Wapiti Valley into Shoshone National Forest (America’s oldest national forest). Teddy Roosevelt once called the broader drive “the most scenic 50 miles in the world.” 

• Engineering landmark: The route was built to reach the dam site. When completed in 1910, Buffalo Bill Dam (originally Shoshone Dam) was the world’s tallest at 325 feet and one of the first major concrete-arch dams in the U.S. It anchors the Shoshone Project, which irrigates tens of thousands of acres in the Bighorn Basin and generates power. 

• Geologic drama: The canyon cuts through ancient Precambrian granite (nearly 2 billion years old) and younger sedimentary layers folded into an anticline. A historical marker notes the Rattlesnake Mountain uplift began about 66 million years ago; the river has been downcutting for the last ~3 million years. 

Autumn color along Historic Route 20 near Epworth, Iowa.
10/01/2026

Autumn color along Historic Route 20 near Epworth, Iowa.

Route 20 used to run through the small hamlet of Forsyth, New York - just east of the Pennsylvania border. The old ali...
09/27/2026

Route 20 used to run through the small hamlet of Forsyth, New York - just east of the Pennsylvania border. The old alignment can be seen on the right side of this picture. Originally, a bridge crossed over the railroad tracks and connected back to the main roadway. Now a circle exists and a small stub of the old road. In the photo you can see the NYS Thruway and Lake Erie in the background. The first white house on the right just beyond the circle was once a gas station.

See the comments for the old bridge crossing.

Nestled in the rolling hills of northwest Illinois, Galena began as a lead-mining boomtown in the 1820s. Named after the...
09/25/2026

Nestled in the rolling hills of northwest Illinois, Galena began as a lead-mining boomtown in the 1820s. Named after the Latin word for lead ore, it quickly grew into one of the busiest ports on the Upper Mississippi, shipping record amounts of lead by steamboat in the mid-1800s. At its peak, the population swelled to around 14,000—briefly larger than Chicago—and the town became home to Ulysses S. Grant and eight other Civil War generals. 

Today, over 85% of Galena is listed on the National Register of Historic Places. Its beautifully preserved downtown—lined with 19th-century brick storefronts along Main Street—sits right along Historic U.S. Route 20 (also known as the U.S. Grant Memorial Highway). This scenic stretch of America’s longest highway winds through the Driftless Area and brings you straight into the heart of a town that feels frozen in time, complete with shops, restaurants, and architecture that have stood for nearly two centuries. 
Stroll the historic streets, explore the DeSoto House Hotel (Illinois’ oldest operating hotel), and soak in the riverside views. Galena is the perfect stop on any Route 20 road trip!

Address

Chester, MA

Opening Hours

Wednesday 11am - 4pm
Thursday 11am - 4pm
Friday 11am - 7pm
Saturday 11am - 5pm

Telephone

+16177335796

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