Sleepy Hollow, New York
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Travel Back in Time in These 12 Historic Towns Across America

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Sleepy Hollow, New York
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Plymouth, Massachusetts
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Plymouth, Massachusetts

Known as "America's Hometown," Plymouth is the oldest community in New England and, of course, the site of the first Thanksgiving. Historic homes such as Harlow Old Fort House, built in 1677, are just the start of the offerings. Plimoth Plantation (which uses an old-fashioned spelling to distinguish the museum from the town) is a replica of what the pilgrim settlement looked like in 1627, right down to characters walking around speaking in the appropriate dialect. And no visit is complete without Plymouth Rock. Masks and social distancing are required at Plimoth Plantation, and some paths have been made one-way.

Related: 20 Things You Never Knew About New England

Boone Hall Plantation
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Mount Pleasant | Charleston, South Carolina

This quaint Southern destination is home to Boone Hall, one of the oldest working plantations in America. While visitors pay up to $26 to tour the 339-year-old plantation — also one of the most photographed in the country — there are a number of free attractions in the area. The "old village" neighborhood is on the National Register of Historic Places and features colonial and antebellum homes that look straight out of the movies. At Boone Hall, there's temperature screening at the front gate, masks and social distancing are required, and some areas on the property will even be “fogged” with disinfectant throughout the day.

Related: 19 Free or Cheap Things to Do in Charleston

Jamestown Settlement, Williamsburg, Virginia
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Jamestown Settlement | Williamsburg, Virginia

Visiting Jamestown Settlement, a re-creation of America's first permanent colony, is like stepping back in time. There are replicas of 17th-century ships and a Native American village to tour — check the website for discounts and deals — along with a whole town to explore. The Memorial Church houses parts of original 17th-century churches. Expect a mask requirement, social distancing rules, and even more outdoor exhibits at Jamestown Settlement. 

Related: The Oldest Building in Each State

Elfreth's Alley, Philadelphia
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Elfreth's Alley | Philadelphia

Dating back to 1720, Elfreth's Alley has been dubbed America's oldest residential neighborhood. Visitors can buy tours to get a glimpse inside private homes, and celebrations feature actors portraying historical figures such as Ben Franklin and Dolley Madison. The Alley has limited days and fewer tickets as it eases back into reopening.

Related: Most Iconic Staircases Around the World

French Quarter, New Orleans
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French Quarter | New Orleans

This National Historic Landmark is New Orleans' oldest neighborhood, founded in 1718, and many of the homes boast centuries-old ironwork and courtyards. There are a number of self-guided walking tours through the neighborhood, including free ones, and plenty of French treats to try along the way.  

Related: 36 Bucket-List Destinations for Music Lovers

Gettysburg, Pennsylvania
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Gettysburg, Pennsylvania

Self-guided walking tours take visitors along streets where President Abraham Lincoln once paraded. A visit to the infamous battlefield is a must for those keen on history, and thrill-seekers can enjoy ghost tours through the "haunted" places of Gettysburg.

Related: 40 Famous People's Homes You Can Visit

Downtown Savannah, Georgia
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Downtown Savannah, Georgia

This scenic neighborhood, a National Historic Landmark District since 1966, is a prime example of old-time Southern architecture. Stroll the cobblestone streets and note the intricate ironwork of mansions restored to the original pink, green, red, and blue of the 18th century.

Related: Where to Relocate If You’re Working Remote Full-Time

Sturbridge, Massachusetts
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Sturbridge, Massachusetts

Sturbridge is home to the largest outdoor history museum on the East Coast. Old Sturbridge Village replicates life in the 1830s, complete with period characters, farm animals, historic buildings, and activities for kids — and because of coronavirus has pivoted by closing most buildings and focusing on exhibits and lessons that can be offered outdoors. (How that works during the worst winter weather has yet to be announced.) Sturbridge is also home to the Tantiusques, an open space reserve on the National Register of Historic Places.

Related: Fun Day Trips for Families in Every State

Sleepy Hollow, New York
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Sleepy Hollow, New York

Sleepy Hollow is steeped in history and charm. The site of the iconic 1790s tale "The Legend of Sleepy Hollow" by Washington Irving, the town dates back to the arrival of Europeans in the 1600s. Visitors wandering the streets enjoy views of the Hudson River and a peek at mansions later built by millionaires such as John D. Rockefeller.

Related: The Best Cheap & Free Stuff New York State Offers

California Street
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Jacksonville, Oregon

This Old West town was the first in Oregon to be added to the National Register of Historic Places. Stroll through town and imagine yourself in the mid-1800s, parking your horse at the water trough, or visiting the local saloon.

Related: 18 Towns Where You Can Still Experience the Wild West

Taos Pueblo, New Mexico
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Annapolis, Maryland
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Annapolis, Maryland

Annapolis is known as "a museum without walls" thanks to its historic downtown area and street plan, established in 1695. Walking through town, visitors can see brick mansions built for founding fathers and wooden houses for colonial merchants. The 18th-century William Paca House, a National Historic Landmark, is just one of the city's points of interest.

Related: The Oldest Bar in Every State