20 Most Beautiful Main Streets in America

Frederick, Maryland

Frederick is a small city in Maryland, and its views of the Blue Ridge Mountains are one of the city’s major attractions. Market Street, one of the most beautiful main streets on this list, is another. The hip-meets-historic vibe of the main drag features murals and art installations, restaurants, boutiques and a huge craft brewing scene. The Delaplaine Arts Center is free to the public, and the North Market Pop Shop sells 400 types of vintage sodas.  

Galena, Illinois

Conforming to the shape of the Galena River, Galena’s main street offers visitors access to a riverfront walkway. The architecture is in the Italianate style, with brick storefronts and bay windows, and trolley cars bring visitors and locals to nearby wineries. A three-hour drive from Chicago, Galena is a great place for a riverside stopover, especially at the DeSoto House Hotel, which has hosted famous guests like Ulysses S. Grant since 1855. 

York, Pennsylvania

Known as the White Rose City, York has revitalized its main street in the past few decades. Market Street is filled with local businesses setting up shop in Victorian and Classical Revival–style buildings, and on the first Friday of each month, the shops stay open late to bring visitors together. One major draw of the downtown area is the Central Market, a York tradition that’s been in business on Philadelphia Street since 1888.  

Cedarburg, Wisconsin

A suburb that feels like a small-town getaway, Cedarburg is about 20 miles north of Milwaukee. The old mill town’s tidy main street offers visitors a chance to pop in and out of shops, inns, cafes, art galleries and museums. Cedarburg has an incredible 200 historic buildings that have been restored, with 8 of them landing on the National Register of Historic Places.

Cape Girardeau, Missouri

Halfway between St. Louis and Memphis, Cape Girardeau gives tired visitors a great place to stay the night. A winner of the Great American Main Street Award, the river town blends historic charm with modern technology, and some of the shops on the main street have been in business for more than 75 years. The small town has 61 structures on the National Register of Historic Places, along with a creative corridor that boasts public art and a children’s museum.

Kent, Connecticut

One of the many towns that has been compared to Stars Hollow, from the Gilmore Girls, is Kent, Connecticut. It has the same charming, small-town appeal, including locally owned stores and town events and festivals. Twinkly lights wrap around charming inns and shops on Kent’s beautiful main streets, lending a cozy New England vibe.

Covington, Kentucky

Located just across the Ohio River from Cincinnati, Covington offers a revitalized Main Street to visitors and locals. Anchored by the Carroll Chimes Bell Tower, Main Street offers a mix of Midwestern and Southern charm in an area that is seeing an influx of independent businesses. Brimming with beautiful Italianate brick buildings and public art, Covington’s Main Street is a great day trip.

Howell, Michigan

For a historic weekend, look no further than Howell, Michigan. Many of the buildings haven’t changed since the city was incorporated in 1863, and Italianate buildings dot the street. Two high Victorian façades, a Victorian Gothic church, a modified English Gothic Church, a Tudor Revival office building and the original Opera House are some architectural standouts.

The main street has dozens of specialty retailers and restaurants, and it also hosts events and festivals throughout the year. With initiatives to encourage residents to buy local, this main street offers both charm and neighborly values. 

Bath, Maine

Bath, Maine, looks just like a cozy New England town should. Gardens, brick buildings and church spires dot the main street, along with a variety of businesses and outdoor spaces. The buildings are a mix of Italianate, Romanesque Revival, Gothic Revival, late Federal and Greek Revival style. The Sagadahoc County Courthouse, an Empire-style building designed by Francis Fassett in 1869, is a notable example. A walking tour of the city is available.

Franklin, Tennessee

With its rustic charm, Franklin looks to distinguish itself from its neighbor Nashville. The city blends historic preservation and modern sophistication: A mix of antique shops, bookstores, fashion-forward boutiques, art galleries and restored homes line Main Street. To explore the district, hop on the city’s charming (and free) green and red trolley, built in the 19th century.

Some of the oldest buildings include those near the public square and courthouse, and you can see how architectural styles changed as downtown expanded its reach. The Downtown Local Historic District is also listed in the National Register of Historic Places.

Staunton, Virginia

One of the oldest towns west of the Blue Ridge Mountains, Staunton remained nearly unscathed by the Civil War. Now, Staunton has six historic districts listed on the National Register of Historic Places, and its Main Street is an eclectic mix of architectural styles designed by local architect TJ Collins from 1891 to 1911. Collins designed or remodeled about 200 buildings in Staunton, many of which are still in use.

Visitors can check out the American Shakespeare Center, home of the world’s only authentic recreation of the Blackfriars Theater; step back in time at the Frontier Culture Museum, an outdoor living history museum illustrating the daily lives of Shenandoah Valley’s earliest settlers; and discover the life and legacy of President Woodrow Wilson at his library and museum.

Woodstock, Vermont

A quaint and quiet town, Woodstock is home to historical brick homes, a covered bridge, a village green and a small main street. Visitors and locals alike can explore the locally owned shops, art galleries and country stores, all within walking distance. There are no big-box retailers in sight! While visitors can take horseback riding lessons in the town, the main street gives off a vibe that horse-drawn wagons aren’t too far in the past.

Silver City, New Mexico

Vibrant and so-very southwest, Silver City’s main street is a colorful array of restaurants, galleries, studios and shops. The main street features some of the 50 murals woven throughout the city. The newly renovated historic Silco Theater, which was built in 1923, is one of the major theater landmarks in the city. A few other theaters make up the Theater District, and the city has hosted its annual Lighted Christmas Parade since 1991. Every year the impressive lighted floats bring around 12,000 people to one of the most beautiful main streets in New Mexico. 

Charleston, South Carolina

The oldest city in the state, Charleston features beautiful homes and gardens along its many tree-lined avenues. History buffs will particularly enjoy Chalmers Street, one of only eight remaining cobblestone streets in the city. The city is also home to the Old Slave Mart, where enslaved people were sold in antebellum-era auction galleries. Now the market serves as a meeting place, and houses a museum where visitors can take a self-guided tour to learn about America’s history of slavery. The museum adds extra context for visitors who tour plantations in the area.

Provincetown, Massachusetts

About 120 miles from Boston, this Cape Cod vacation town is known for its vibrant arts scene and friendliness to the LGBTQ+ community. The main drag, Commercial Street, is one of Massachusetts’s most beautiful main streets, with a small-town feel and Queen Anne–style buildings. Homes, bed and breakfasts, art galleries, shops and restaurants mix seamlessly on this bustling main street.

Ogden, Utah

Known as Salt Lake City’s devious little sister, Ogden’s Historic 25th Street was once home to brothels, political scandals and gang rivalries. Now, one of the most beautiful main streets in the Rocky Mountains brings together more than one million travelers, art collectors and food and outdoor enthusiasts each year. Ogden’s event calendar is packed, with art gallery exhibits open nearly every day, and it’s also the site of major athletic events. Famous figures have paraded along 25th Street, such as Presidents Taft, Hoover and Teddy Roosevelt, along with William “Buffalo Bill” Cody. 

Georgetown, Washington, D.C.

Bustling M Street in historic Georgetown features packed sidewalks, high-end stores and charming cobblestone streets. The neighborhood is home to the world-class university, making it one of the best college towns in the country. Make sure to check out historical standouts on M Street, including Old Stone House, a pre-Revolutionary War home and one of the oldest buildings in the District.  Next, head over to Georgetown’s most famous movie set: the terrifying stone steps from The Exorcist.

Fort Pierce, Florida

Fort Pierce has seven buildings on the National Register of Historic Places, including the Sunrise Theatre, Moore’s Creek Bridge and the original Seminole War–era Army post that gives Fort Pierce its name. There’s also a ghost walking tour through the historic area! Events like the town’s annual celebration, Friday Fest, and its annual reverse raffle auction keep the downtown area lively. Fort Pierce also has a hugely popular farmer’s market, which brings nearly 5,000 people to the main drag on Saturdays.

Paso Robles, California

Once located near natural hot springs, this wine-country town has a beautiful main square that offers visitors everything from a movie theater and exhibits to restaurants and boutiques. Wine tastings are prevalent in the main square, which is dotted with buildings in various styles such as high Victorian and Mexican adobe.

Ridgewood, New Jersey

Ridgewood’s family-friendly main street is densely packed with a movie theater and numerous boutique shops and restaurants. East Ridgewood Avenue is the main artery, connecting the downtown historic district to modern accommodations. Some standout structures are the late-18th-century Archibald-Vroom House—the oldest building in the village—and the sprawling California Mission Revival-style train station, a historical landmark an hour from midtown Manhattan. The train station dates back to 1916 and is listed on the national and state Register of Historic Places.

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Sources:

• Cedarburg, Wisconsin: “History of Cedarburg”
• The Old Slave Mart Museum: “Home”
• Delaplaine Arts Center: “Everyone Deserves Art”
• North Market Pop Shop: “Home”
• DeSoto House: “Galena, Illinois”
• Central Market: “Enjoy a Market Morning”
• Village of Ridgewood: “Welcome to Ridgewood”
• Downtown Franklin Association: “Explore America’s Favorite Main Street District”
• Mainstreet.org: “Past Recipients”
• Fort Pierce Farmers Market: “About”
• The Silco Theater: “An Art Deco Gem in the Heart of Historic Silver City, New Mexico”