Step Back Into Time at These Historic Holiday Destinations

For many, the holidays are about traditions—not just personal family activities, but local events and cultural practices that set this time of year apart. Across the country, destinations come alive with festive events honoring the heritage of a community, historic landmarks put on enchanting and educational experiences, and sacred holidays are once again celebrated with reverence. Visit the destinations below and take a magical winter tour through the ages: beginning in the Spanish settlement of 1500s-era Florida and the British colonies of 1700s-era Virginia, to the towns founded by European immigrants and the 19th-century frontier outposts of the Old West.

St. Augustine remembers its Spanish settlement roots throughout the year – courtesy of Florida’s Historic Coast

When Don Pedro Menendez de Aviles landed on the shores of St. Augustine, Florida in September of 1565, his mission’s priest, Father Francisco López de Mendoza Grajales, conducted what was to be the first parish mass in the New World. This holy site is where the new Spanish settlers would begin devotion to Our Lady of La Leche. Today, a small mission chapel stands in honor of Our Lady of La Leche. “Noches de Navidad” and Las Posadas will take place from 3 to 9 p.m. on December 16th, 2023. The event features a live Nativity, Eucharistic Adoration, cookies, hot cocoa, and a 16th-century Spanish procession of “Las Posadas” (the Inns). Admission is free, but reservations are required.

Many local events celebrate the traditions of the European settlement, including St. Augustine’s famous Night of Lights. It is firmly rooted in the Spanish tradition of displaying white candles in their windows during the holiday season. For images to accompany postings click here. More Spanish influence and heritage can be found throughout Florida’s Historic Coast. The St. Augustine Spanish Food & Wine Festival celebrates the food, wine, and culture of Spain with a multi-day festival. Foodies, history buffs, and xenophiles can explore Spanish history and traditions while enjoying Spanish wine, tapas, and spirits. The festival takes place on the Flagler College Campus the last weekend in February.

Aerial view of the Governor’s Palace in Colonial Williamsburg by Eric Foster – Unsplash

The holidays are a wonderful time to visit the “Historic Triangle” in Virginia, when Williamsburg, Jamestown, and Yorktown light up with seasonal decorations, markets, and entertainment. Historic hotels, estates, and inns throughout the region sparkle with traditional lights and décor throughout the Christmas season. A Williamsburg White House Inn, themed after the White House, is draped in holiday decorations. And Colonial Williamsburg Resorts is celebrating the holiday season with a festive array of events and experiences including the Annual Lighting Ceremony at the iconic Williamsburg Inn and the highly-anticipated Annual Gingerbread Open House at the Williamsburg Lodge.

On December 1st, the Yorktown Christmas Tree Lighting takes place at Victory Walk and Riverfront Landing. The evening is filled with live music including a performance by the Fifes and Drums of York Town. A procession will then make its way from the Victory Monument to Riverwalk Landing, where the tree lighting ceremony takes place. The following day, the Yorktown Holiday Boat Parade features a fleet of decorated boats navigate around the York River and compete for best in show. Festivities include caroling around a beach bonfire, a musical performance by the Fifes & Drums of York Town, and complimentary hot cider. The boats finish the evening as they make their way down the river in a dazzling show of lights. Also in Yorktown, Christmas Market on Main returns to historic Main Street on December 2nd and 3rd. Close to 100 vendors line the street selling everything from nautical paintings to handmade soaps to Christmas wreaths! The Town Crier will ring in the market, followed by a performance from the Fifes and Drums of York Town, an appearance by Santa Claus himself, and musical entertainment throughout the day to add to the festive atmosphere.

On December 2nd, 9th, and 16th, Colonial Williamsburg’s Grand Illumination lights up the night sky over the colonial capital. Visitors can begin the special day by checking out the unique decorations throughout the Historic Area. Then, enjoy musical performances on multiple stages throughout the streets and fireworks displays from the Capitol and the Palace.

At the Williamsburg Christmas Market dozens of vendors sell holiday gifts and décor, while shoppers enjoy photo ops with Santa, live entertainment, gluhwein (warm spiced wine), craft beers, Christmas music, fire pits, and delicious market food from local restaurants.

On December 9th, visitors can enjoy “At Christmas be mery”: A Special Evening at Historic Jamestowne. Guests join an early Virginia Christmas celebration complete with costumed interpreters, madrigal singers, a seasonal bonfire, and caroling, along with a musical performance by William and Mary’s Christopher Wren Singers. From December 16th to 31st, visitors will celebrate 17th– and 18th– century holiday traditions through festive interpretive programs, traditional cooking, caroling, and musical entertainment at Christmastide in Virginia at Jamestown Settlement.

An historic home in Natchez, Mississippi decorated for Christmas – courtesy of Lou Hammond Group

Natchez, Mississippi, known for its Southern hospitality, historic homes, and significant architecture, invites visitors to avoid the crowded cities this holiday season and swap snow for sunshine in this quaint riverside town. With mild winter temperatures and a selection of holly jolly happenings, including colored lights covering Main Street, decorated historic home tours and more, Natchez is the ideal place to create lasting memories for the whole family.

Natchez has over 1,000 structures listed on the National Register of Historic Places. Do You See What I See? Christmas tours at Sunnyside takes visitors through each room in the historic house, decorated with over 30 Christmas trees. Jeweled Christmas Tours, located in The Towers Mansion, adorns its halls in thousands of shimmering jewels in a showing named one of the top 10 most unusual Christmas displays by USA Today.

Natchez Garden Club’s Christmas Tours offer a delightful blend of tradition, history and holiday cheer, allowing guests to immerse themselves in the unique yuletide charm of Natchez. Beloved historic homes, including Magnolia Hall, Monmouth Historic Inn and Dunleith Mansion, make spirits bright when they open for Christmas tours. These homes will deck the halls this holiday season for guests from all over to admire the classic estates and festive decorations.

In partnership with American Queen Voyages, Christmas in Natchez will bring a festive European-style Christmas market to town for a month-long celebration at the Natchez Christmas Village Markets. Guests are invited to shop their way through the festive stalls, where they will find local crafts, seasonal treats and unique holiday gifts, perfect for checking off holiday shopping lists. Don’t forget to stop by Hal Garner at Nest for stunning antiques and home collectables, or spend the day wandering the city’s many other shops.

A journey to Mainstrasse Village in Covington, Kentucky transports travelers to a 19th century Germantown where they can enjoy an eclectic array of German-inspired shopping, cuisine, and entertainment. On December 3, this serene village undergoes a magical transformation into the enchanting Mainstrasse Christkindlmarkt. From 8:00 a.m. to 2:00 p.m., indulge in the perfect fusion of Old-World charm and 21st-century vibrancy at this German-inspired holiday market. The event showcases skilled creators, delectable treats, mesmerizing music, and more. Don’t miss this opportunity to explore the Christmas market and uncover unique gifts for your loved ones.

A cold day outside in Morrison, Colorado by Gennady Zakharin – Unsplash

Colorado is already an excellent choice for winter travelers looking for a magically snowy paradise. Head to Denver first, and sxperience the unique charm of the holiday season before 1924 by touring the beautifully decorated Center for Colorado Women’s History and enjoying a delightful tea service during their Holiday Tea special events (November 25th – December 16th).

From Denver, you’ll have easy access to a number of enchanting mountain towns in the Rockies. For a cozy and rustic adventure, 2 Below Zero in Frisco offers mule-team-driven sleigh rides with chuckwagon dinners and live music, while Steamboat Springs provides a Wild West touch with its Haymaker Sleigh Ride Dinner.

In Morrison, the historic Fort Restaurant, designed to resemble an 1800s fur trading post, offers a unique holiday dining experience serving traditional dishes like bison and game meats. Tesoro Cultural Center’s Las Posadas (December 24th) is an annual Christmas Eve celebration that reenacts Mary and Joseph’s journey to Bethlehem, featuring children’s participation, traditional music, piñatas and complimentary treats like biscochito cookies and Mexican hot chocolate.

Visit Cripple Creek as the Gold Camps come alive with dazzling holiday lights adorning mine headframes (November 24th – December 31st). Enjoy a festive self-guided tour, complete with holiday music and beautiful light displays in this historic mining region.

For a touch of nostalgia, Colorado’s many historic trains take travelers on a journey through winter wonderlands. The Leadville Railroad Holiday Express offers a magical ride through snowy mountains with scenic views. The Santa Express Train with the Royal Gorge Route Railroad leads passengers to the North Pole and back, complete with a visit from Santa. The Polar Express Train Rides at the Colorado Railroad Museum and the Durango & Silverton Narrow Gauge Railroad, both offer unparalleled holiday experiences. The Georgetown Loop Railroad’s Winter Holiday Trains are one of Colorado’s most authentic living history experiences and offer timeless adventures through scenic vistas decorated with more than 300,000 holiday lights.

On the eastern side of the state, at Bent’s Old Fort, visitors can step back in time on December 3rd to experience the 1830s and 1840s with activities like reading “A Christmas Carol,” trading for taffy and playing traditional card games. Scheduled programs include a Yule Log tradition demonstration and learning about the weapons used in the Borderlands that provide a glimpse into the past.

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