The Prettiest Town Squares in the U.S.
The Prettiest Town Squares in the U.S.

Since the dawn of modern city planning, town squares have been a vital part of the urban social scene. A place to gather, hold festivals and important meetings, seek entertainment, or simply spend time in nature, town squares often set the scene for life in rural America. From Gilmore Girls' Stars Hollow to every Hallmark holiday movie, iconic depictions of pretty town squares are quintessential in American pop culture and it’s no wonder a quaint city center is synonymous with the image of small town USA. Link arms and come stroll with us in the prettiest small town squares in the U.S.

Plaza Park, Healdsburg, CA

Aerial of Park Plaza in Healsburg, showing trees, walkways, a fountain, and gazebo.
Credit: John D. Ivanko/ Alamy Stock Photo

The picturesque Plaza Park in Healdsburg, California is a true testament to the iconic American town square. A stately gazebo, surrounded by ancient oak trees, crowns the center of Plaza Park and welcomes visitors from far and wide. Healdsburg was originally founded by gold miners in the mid-1800s. Now the area's claim to fame is the gorgeous Sonoma wine country, which draws in visitors seeking the country’s best vintages. Charming restaurants and accommodations line the park, making it a great base for exploring the vineyards by day and cozying up in a romantic B&B by night. Aside from being a bustling wine-o destination, Healdsburg prides itself on cultivating a tight-knit community and holds various events like the annual “Picnic in the Plaza,” a giant potluck spanning the entire park.

Wright Square, Savannah, GA

Wright Square, Savannah Georgia with large overhanging oaks, grass and walkways
Credit: John Wijsman/ Shutterstock

Wright Square in Savannah, Georgia is dripping with history, much like the city itself. One of 22 squares in the city, Wright Square is the second oldest in Savannah and named after Sir James Wright, the last Royal Governor of Georgia. The square is home to two separate monuments, a grand statue, and a boulder. The statue honors William Washington Gordon, who founded the Central Georgia Railroad, while the boulder has a more interesting backstory. The original boulder was erected to honor Tomochichi, a Yamacraw man who was an ally of General Oglethorpe. The two are said to have been the founders of Georgia itself. Tomochichi requested to be buried here after his death in 1737. Unfortunately, the original grave marker was removed to make way for Gordon’s grand statue until his daughter-in-law, Nellie Gordon, stepped up in 1899. She, along with the Colonial Dames, selected the boulder which serves as Tomochichi’s gravemarker and placed it where it lies today.

Heritage Square, Flagstaff, AZ

Benches and buildings in Flagstaff’s Heritage Square.
Credit: Bill Miller/ Alamy Stock Photo

Reminiscent of a classic Western town, Flagstaff’s Heritage Square speaks to the city’s history. Heritage Square’s mission is to provide free entertainment for the city, holding countless complimentary art shows, concerts, and community events in its unique, open-air amphitheater throughout the year. Several historic buildings line Heritage Square including Hotel Monte Vista and Babbitt's Backcountry Outfitters. It’s said that tunnels were dug under the city in the late 1800s and both of these buildings still have access to them. Bordering the square's southern edge is the Southside neighborhood which is home to trendy restaurants and craft breweries, perfect after a long day traipsing the town or skiing at nearby Snowbowl.

Mallory Square, Key West, FL

Aerial of Mallory Square, Key West.
Credit: Felix Mizioznikov/ Shutterstock

Named for the “First Lady” of Key West, Ellen Mallory, and her senator son, Mallory Square has been a stomping ground for famous names (including Mark Twain and Tennessee Williams) for decades. Today it is the beating heart of Key West’s downtown and features a sculpture garden devoted to Key West’s notable residents. Mallory Square is perhaps most famous for what is known as the “Sunset Celebration” when visitors flock to the square to watch the sunset over the Gulf of Mexico. What started as a niche tradition has grown into a carnival-like atmosphere with entertainers, art vendors, and food trucks, a true celebration in the “Conch Republic.”

Village Square, Solvang, CA

Danish style buildings and windmill on street in Solvang.
Credit: fox_lei/ Shutterstock

The village square in Solvang, California is something straight out of the Danish countryside. Although originally a Spanish settlement that was abandoned after the Mexican War of Independence, Solvang was founded by immigrants from the Netherlands in 1911 who brought not only their Danish heritage but also their half-timbered architecture and, most importantly, æbleskivers, delicious Danish pancakes. The Village Square is the touristic heart of Solvang and is home to various cafes, bakeries, and other small shops. Nestled in the Santa Ynez Valley, Solvang is a great location to visit not only for its quaint, European feel but also for its proximity to a burgeoning wine region.

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