10 charming town squares to visit this fall

October 8, 2019 // By Priscilla Blossom

By Priscilla Blossom
Travel Expert October 8, 2019

Picturesque town squares get even better in autumn Photo courtesy of iStock / RobertCrum

Picturesque town squares get even better in autumn

Autumn often brings about some of the most festive outdoor celebrations: pumpkin patches and corn mazes, plus the final days of farmers' markets and outdoor concerts just before the snow. And with the intense summer heat winding down and the crisp, cool fall air coming in, you’ll likely find yourself excited to attend some of these. Such activities often pop up all around a large city, but when you live in a smaller town, they can often be found right in the center, at the town square or plaza. We’ve rounded up some of the most interesting and picturesque town squares all around the country that are worth checking out.

Healdsburg Plaza | Healdsburg, California Photo courtesy of Barbara Bourne

Healdsburg Plaza | Healdsburg, California

Charming boutique shops, vibrant art galleries and exceptional cafes and restaurants all line the streets surrounding Healdsburg Plaza. Being in Sonoma County, you'll also find a number of wine tasting rooms (like Thumbprint Cellars), though you’ll definitely want to wander outside the plaza later to check out some of the amazing wineries in the area such as Jordan Winery. Drop by the plaza during a concert or festival, or simply pick up a coffee at Flying Goat, then find a bench to sit on and enjoy the scenery.

Santa Fe Plaza | Santa Fe, New Mexico Photo courtesy of Tourism Santa Fe

Santa Fe Plaza | Santa Fe, New Mexico

This historic plaza in the heart of magical Santa Fe is host to numerous festivities throughout the year, from the annual Spanish Colonial Arts Society’s Spanish Market to the Holiday Lighting event every November featuring hundreds of farolitos (paper bags lit by votive candles). The Palace of the Governors is on the north side of the plaza; it’s a museum dedicated to Santa Fe’s history that also serves as the venue for an open-air market featuring local Native American craft vendors. And if you feel peckish, make sure to grab a bite at one of the popular local food carts like Mafé Cafe or Roque’s Carnitas.

Wright Square | Savannah, Georgia Photo courtesy of Visit Savannah

Wright Square | Savannah, Georgia

While some of Savannah’s other town squares might hold a bit more popularity, Wright Square and its surrounding area are equally worth your time and attention. Aside from being the perfect place to sit or stroll underneath the shade of large, majestic oak trees, it’s also the site of the grave and monument to the Yamacraw leader, Tomochichi – without whom there would likely be no Savannah in the first place. And if you make it to town for the fall, don’t forget to checkout nearby events like the Savannah Speed Classic, SCAD’s Savannah Film Festival and the Savannah Food and Wine Festival.

City Square Park | Oskaloosa, Iowa Photo courtesy of Oskaloosa Main Street

City Square Park | Oskaloosa, Iowa

Featuring a historic bandstand at the heart of it, Oskaloosa’s City Square Park is pure Americana. Townsfolk crowd the greens here in the summer for farmers' markets and events like Art on the Square, and the Annual Lighted Christmas Parade in the winter. But we find the beautiful orange, red and brown leaves truly brighten up the square in the fall – and so do the kiddos who love to trick-or-treat in the area.

Jackson Hole Town Square | Jackson, Wyoming Photo courtesy of iStock / nycshooter

Jackson Hole Town Square | Jackson, Wyoming

See the American West come alive in Jackson Hole Town Square, where carriage rides and Old West shootout reenactments enchant visitors and locals alike. The square features distinctive antler arches in each corner, with art galleries, outlet shops, restaurants and bars all along each side. And just off into the distance, nothing but magnificent mountains and beautiful open spaces.

Woodstock Square | Woodstock, Illinois Photo courtesy of City of Woodstock

Woodstock Square | Woodstock, Illinois

You might remember Woodstock Square from the film "Groundhog Day," but this square offers so much more all year long –farmers' markets, car shows, charity walks and more. You can enjoy annual events such as the Wizards and Witches of Woodstock, plus Halloween festivities in late October. The Lighting of the Square in November also draws crowds in autumn. The historic square is surrounded by lush trees and gorgeous, late 19th-century Victorian buildings, including the Woodstock Opera House.

Heritage Square | Flagstaff, Arizona Photo courtesy of Discover Flagstaff

Heritage Square | Flagstaff, Arizona

Heritage Square is home to Flagstaff’s only open-air amphitheater and serves as the cultural hub of the downtown area. Live music, movies, dance performances, art shows and other enriching activities happen here and draw in locals from all walks of life. Certainly a more modern town square than some of the others on this list, Heritage Square features plenty of chains along with smaller, local businesses on its outskirts, including the Flagstaff Chocolate Company.

Village Green | Bar Harbor, Maine Photo courtesy of Visit Maine

Village Green | Bar Harbor, Maine

This idyllic green space in Bar Harbor, Maine features everything you'd want from a public square: a historic town clock, plentiful benches, a whimsical gazebo and even a bronze fountain for making wishes. What’s more, there are plenty of delightful small businesses surrounding it, from ice cream parlors to pottery stores. Additionally, Village Green serves as a starting point for a day trip into nearby Acadia National Park, thanks to the park’s shuttle service.

Old Town Square | Fort Collins, Colorado Photo courtesy of Richard Haro

Old Town Square | Fort Collins, Colorado

Imaginative sculptures, energetic street performers and romantic Tivoli lighting all set the mood at Old Town Square in northern Colorado. In the summers, you’ll find families cooling down in the splash pads, while the winters bring young and old alike taking turns on the ice skating rink. And those who prefer neither can always do a bit of shopping at places like Rocky Mountain Retro, Old Firehouse Books, and Curiosities. Add to that a brewery, bakery, artist co-op and an arcade, and you’ll wonder why you ever have to leave.

Mallory Square | Key West, Florida Photo courtesy of E+ / worldofphotos

Mallory Square | Key West, Florida

For an entirely different sort of town square experience, you need to check out Key West’s Mallory Square. Filled with arts and crafts vendors, eateries of all kinds and live entertainment daily, this square is a place frequented by tourists while still beloved by locals. After all, who couldn’t love epic sunsets like the ones seen here every night?

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About Priscilla Blossom

Pris Blossom is a freelance writer and feminist mama with a love for travel, writing, music, film, yoga, museums, cultural anthropology, and her awesome kid. Read her words at PrisBlossom.com.