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20 Most Beautiful Main Streets in America

There's nothing better than strolling down a cute main street in a new town. But where should you go? Here are 20 of the most beautiful main streets in America.

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Main Street, U.S.A.

It may seem like the quaint, charming American Main Street is a thing of the past—but these 20 beautiful streets in towns from sea to shining sea prove that that’s not the case! You’ll want to stroll down these picturesque main streets. Plus, check out the most charming small towns in every state.

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The Old train station, Kent, Connecticut, USA
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Kent, Connecticut

One of the many towns that has been compared to Gilmore Girls‘ Stars Hollow is Kent, Connecticut. It has the same main street appeals, including locally owned stores and town events and festivals. Twinkly lights wrap around charming inns on Kent’s main street, giving off a cozy New England vibe. These are the nicest places in every state in America.

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The old mill in Cedarburg Wisconsin is not a working mill any longer but still hosts a series of activities and shops.
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Cedarburg, Wisconsin

A small-town getaway, Cedarburg is about 20 miles north of Milwaukee and offers visitors a chance to walk down the main street and pop in and out of shops, inns, cafes, and art galleries and museums—many of which are nestled inside historic buildings.

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View from Annapolis Rocks, along the Appalachian Train on South Mountain, Maryland.
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Frederick, Maryland

Frederick is the third-largest city in Maryland and its views of the Blue Ridge Mountains are one of the major attractions. The beautiful main avenue, Market Street, is another. The hip-meets-historic vibe of the main street features churches and shops like The North Market Pop Shop, which sells 400 types of vintage sodas. Do you know where to find the best coffee shop in your state?

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Illinois, Galena, Historical town of Galena along main street.
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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. Trolley cars bring visitors and locals alike to nearby wineries. A three-hour drive from Chicago, Galena is a great place for a riverside journey, especially at the DeSoto House Hotel, which has hosted guests like Ulysses S. Grant since 1855. Check out the funniest street names in every state.

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market street
Courtesy Downtown inc

York, Pennsylvania

Known as the White Rose City, York has seen a revitalized 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 of the major attractions on Market Street is the Central Market, which has been in business since 1754.

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Ridgewood Station in New Jersey in Cold winter day

Ridgewood, New Jersey

Within the family-friendly neighborhood, Ridgewood’s 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, where commuters can get into midtown Manhattan within an hour. The train station dates back to 1916 and is listed on the national and state Register of Historic Places. If you love history, you’ll want to check out the most historic landmark in every state.

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CAPE GIRARDEAU,MO, USA - NOVEMBER 20, 2017: Downtown during Christmas decoration in Cape Girardeau, Missouri, United States
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Cape Girardeau, Missouri

Halfway between St. Louis and Memphis, Cape Girardeau gives tired visitors a great place to stay the night—or two. 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 city has 57 registered structures on the National Register of Historic Places, along with a creative corridor that boasts public art and a children’s museum. This is how every state in America got its name.

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Covington, Kentucky, USA-June 14, 2013: towers in Covington next to the Ohio river during the blue hour. June 14, 2013 in Covington, Kentucky.
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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.

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Architecture in Michigan,USA,architecture in the snow day at Michigan,Winter in Michigan
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Howell, Michigan

For a historic weekend, look no further than Howell, Michigan. Many of the buildings have not been changed since the city was incorporated in 1863, and the 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 more than 40 specialty retailers and restaurants, and it is also the location for many events and festivals throughout the year. With initiatives to encourage residents to buy local, this main street offers both charm and neighborly values. Here are some more of the nicest small towns in America.

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The Portland Head Light in Portland, Maine, USA

Bath, Maine

Bath, Maine, looks like what you would imagine a cozy New England town to be. 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, with some notable buildings like the Sagadahoc County Courthouse, an Empire-style building designed by Francis Fassett in 1869. A walking tour of the city is available, a good way to keep your spirits high during your trip. Here are some more small American towns you’d swear were in Europe.

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FRANKLIN, TN-JUNE 29, 2016: Downtown Franklin, voted one of the best towns to live in America.
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Franklin, Tennessee

Not without rustic charm, Franklin looks to distinguish itself from its neighbor Nashville. The city has a blend of historic preservation and modern sophistication, with a mix of antique shops, gift and bookstores, fashion-forward boutiques, art galleries, and restored homes that line Main Street. The city offers free rides in a charming green and red trolley to explore the district, built in the 19th century. Some of the oldest buildings include the public square and courthouse, and the architectural styles differ as downtown expanded its reach. The Downtown Local Historic District is also listed in the National Register of Historic Places. If you love to read, you’ll definitely want to check out the most beloved bookstore in your state.

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Staunton virginia
courtesy woods pierce/Staunton CVB

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, with an eclectic mix of architectural styles designed by TJ Collins from 1891 to 1911, showcases the compactness of the 19th century. 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.

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Quaint shops along Main Street, Woodstock
John Greim/Shutterstock

Woodstock, Vermont

A quaint and quiet town, Woodstock is home to a myriad of historical brick homes, a covered bridge, village green, and a small main street. Visitors and locals alike can explore the small, 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. Check out these astonishing facts about each of the 50 states.

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Silver City, New Mexico USA - July 23, 2007: Bullard Street in downtown Silver City is a charming and interesting look at an old western town, full of shops, stores and restaurants.

Silver City, New Mexico

Vibrant and so-very southwest, Silver City’s main street is a colorful array of restaurants, galleries, studios, and shops. Listed as one of the 100 Best Art Towns in America, 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, with some undergoing renovations. The city has also hosted its annual Lighted Christmas Show since 1991, which displays impressive lighted floats and brings around 12,000 people to the main street each year. Take a step back in time in the oldest historic town in every state.

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Historical downtown area of Charleston, South Carolina, USA at twilight.

Charleston, South Carolina

Teaming with Southern charm, Charleston is brimming with beautiful homes and gardens along its charming avenues. History buffs will particularly enjoy Chalmers Street, one of only eight remaining cobblestone streets in the city. It also features the Old Slave Mart Museum, a massive structure where enslaved people were sold off to work on plantations at the Antebellum Slave Auction Gallery. Now, the market serves as a meeting place for sellers to hawk their goods, and visitors can take a self-guided tour to learn about America’s history of slavery. The museum adds extra context for visitors who tour homes of plantation owners after the fact. Consider a trip—or even moving!—to these small U.S. towns that are about to get more popular.

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Cape Cod, Massachusetts - September 2017: Main street of Provincetown
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Provincetown, Massachusetts

About 120 miles from Boston by car, this Cape Cod vacation town is known for its vibrant arts scene and friendliness to the LGBT community. Commercial Street, the town’s main street, has cute buildings in the Queen Anne style to denote that the beach is nearby. Homes, bed and breakfasts, art galleries, shops, and restaurants mix seamlessly on this bustling main street.

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OGDEN, UT - AUG 24: Treehouse Museum in Ogden, Utah, as seen on Aug 24, 2017.
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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, 25th Street brings together more than one million travelers, art collectors, and food and outdoor enthusiasts each year. The event calendar is packed, with art gallery exhibits open nearly every day and major events like Xterra USA Championship and USA Cycling Masters Road Championships taking place. Famous figures have also paraded along 25th Street, such as Presidents Taft, Hoover, and Teddy Roosevelt, along with William “Buffalo Bill” Cody. You won’t believe these funny town names from every state are real.

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Street scene in Georgetown, Washington, D.C., USA (09/21/2008)

Georgetown, Washington, D.C.

Take a stroll down bustling M Street and take in the sights: Packed sidewalks (on the weekends, mostly), stores like Urban Outfitters, Lululemon, and Kate Spade New York, and cobblestone streets. The neighborhood is home to a world-class higher education institution, making it one of the best college towns in the country. Make sure to check out to historical standouts on M Street. The first is Old Stone House, a pre-Revolutionary War home and one of the oldest buildings in the District. Despite being operated by the National Park Service, it’s one of the District’s most haunted locales. The second, made famous by The Exorcist, is the terrifying stone stairs that joggers and movie buffs frequent. Do you know the most famous movie set in your state?

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way to Fort Pierce beach Florida USA bright blue sky
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Fort Pierce, Florida

On the verge of discovery, Fort Pierce has been compared to other notable small towns with charming main streets. Main Street, Fort Pierce has seven National Register of Historic Places locations downtown, which includes the Sunrise Theatre, Moore’s Creek Bridge, and the site Fort Pierce is named for, the original Army post during the Seminole War. 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, along with a farmer’s market—one of the largest in the state—that brings nearly 5,000 people to the main street on Saturdays.

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New vineyards and wineries on the scenic hills of the California Central Coast where vineyards grow a variety of fine grapes for wine production, near Paso Robles, CA. on scenic Highway 46.
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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. Most importantly, wine tastings are prevalent in the main square, which is dotted with buildings in various styles such as high Victorian and Mexican adobe. Next, find out the small towns you should add to your 2020 travel list.

Amanda Eisenberg
Amanda Eisenberg is a New York City-based journalist. She's covered everything from unlawful nursing home discharges in Maryland to excess helicopter noise in Hoboken. Her work has appeared in The Washington Post, Elle Decor, McClatchy-Tribune Wire Service and dozens of other publications. She has a bachelor's degree in journalism from the Philip Merrill College of Journalism at the University of Maryland (go Terps!). In her free time, Eisenberg enjoys traveling, volunteering and cliff diving. She can be reached at [email protected]