America’s Most Beautiful Main Streets

Leave it to a town with a world-famous Shakespeare festival (seriously, Bing Crosby was the honorary director of the Oregon Shakespeare Festival from 1949-1951) to have a sonnet-worthy Main Street. Set along rushing Ashland Creek and between the Siskiyou mountains, Ashland, Oregon is as charming as they come. Stop in at farm-to-table Lorella Ashland for halibut with shaved fennel and yuzu viniagrette, then hit the town's boutiques.Our favorites: the 4,000-square-foot flagship Papaya Living, stocked with the brand's gorgeous stationery, and Prize, which sells vintage housewares and one-of-a-kind French candy (we love the fleur de sel turtles).

Your first stop on Fort Collins' picturesque Main Street: The Still Whiskey Steaks, where meats are marinated for days in whiskey and happy hour includes fondue and bacon-loaded potato skins and garlic and white wine-steamed mussels. You can work off lunch with a stroll along the drag, stopping in Akinz, in the Old Town Square, for made-in-Colorado T-shirts, tanks, hats and accessories.

If you've ever seen A River Runs Through It, you know Missoula is one of the prettiest corners of the Northern Rockies. The college town's Main Street, Higgins Avenue, is part of what makes the town so cinematic: it's like the set of a Wild Western come to life. Shop historic Butterfly Herbs for huckleberry tea, hit the weekend Farmers Market, and go for dinner at Plonk (the grilled Colorado lamb, with risotto and blacked cherry tomatoes, will get you pumped for the morning hike up to Mount Sentinel).

The town of Washington Depot was supposedly the inspiration for Gilmore Girls (the only thing missing is Luke's Diner). Surrounded by rolling hills, the main drag of Green Hill Road is seriously charming, with its 60-year-old Hickory Stick Bookshop; the gourmet kitchen shop and cafe, The Pantry; and the Valley Spirit Wellness Center.

RELATED: The Cutest Small Towns in the Northeast

Just an hour and a half from Austin in Texas wine country, you'll find the town of Fredericksburg, or "Fritztown." The region was largely settled by Germans in the 19th-century and the European influence remains. You can see in on Main Street, where Silver Creek offers an al fresco beer garden and "tex-clectic" fare like sauerbraten short ribs and Bavarian jaeger schnitzel; Das Peach Haus is known for its roasted raspberry chipotle sauce; and Der Kuchen Laden specializes in kitchen wares from top-notch brands like Wusthof.

In the last few years, Cold Spring has gotten...well...cool. Barber & Brew opened on Main Street in June, with hipsters coming for straight razor shaves and Hudson Valley IPA's in the adjacent bar. Nearby, the wood-walled Old Souls sells outdoor gear with a heavy dose of Americana (and a scent of pine needles and woodsmoke in the air). And if you need your small town with plenty of coffee shops, there are more than enough places for a caffeine fix, from The Pantry and Cuppocino Cafe to the Gourmet Whaler.

RELATED: Your Perfect Catskills Vacation

​

Savannah's Oglethorpe Avenue may be the prettiest street in the entire country—all Spanish moss dripping over centuries-old manses. It's also home to the Juliette Gordon Low Birthplace (founder of Girl Scouts); Collins Quarter (a new Australian coffee shop that's perhaps the South's best source for a matcha latte, steamed with coconut oil honey and orange); and the brand new jewelry shop, 13 Secrets, which features the work of local designers.

RELATED: America's Coolest Southern Towns