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6 Charming Towns to Visit for the Holidays

During the holidays, there are just some places that give you a festive feeling of delight. Whether there are decorations galore, friendly faces with welcoming smiles, or wintery weather with lights all aglow, each of these U.S. towns truly embody the holiday spirit with a charm all their own.

Winni Wanderer | Boothbay, Maine

Boothbay, Maine

Head to Boothbay, Maine for holiday festivities in a town that has a strong maritime history and a population of just over 3,000 residents. This quaint town transforms in early November with greenery, lights, and events that would make the North Pole jealous. At the Harbor Lights Festival, Santa and Mrs. Claus along with other holiday characters (including a lobster!) arrive by boat to bring holiday cheer. On the weekends, climb aboard the North Pole Express at the Boothbay Railway Village, visit the Coastal Maine Botanical Gardens during their Gardens Aglow event that boasts over 600,000 holiday lights, or brave the chilly waters for the Penguin Plunge to help raise funds for the aquatics program which offers free swimming lessons to Boothbay youth.

Jingle all the way to Boothbay


Winni Wanderer | Portsmouth, New Hampshire

Portsmouth, New Hampshire

As the third oldest city in the country, Portsmouth is a city steeped in history - and when it comes to the holiday season, it transforms into a charming vintage wonderland. With the downtown area lit up and decorations on every corner, it truly becomes a place that brings cheer to the season. Must-do events include: a Santa Sunday Brunch (held every Sunday throughout the season) and an Illumination event (both held at the stunning Wentworth by the Sea resort), the 32nd Annual Gingerbread House Contest and Downtown Scavenger Hunt, the 43rd Annual Candlelight Stroll at the Strawberry Banke Museum, and the Holiday Pops Concert at the Portsmouth Symphony Orchestra. All this plus the wonderful shops and community events make Portsmouth a beautiful location to visit for the holidays.

Deck the halls in Portsmouth


Winni Wanderer | Asheville, North Carolina

Asheville, North Carolina

Nestled in the Blue Ridge mountains, Asheville takes southern Christmas festivities to a whole new level. One of the most famous holiday places to visit is the Biltmore Estate which features more than 100 hand-decorated trees and 1,000 feet of fresh greenery. The Biltmore Estate was also the site of the Hallmark Channel movie “A Biltmore Christmas” filmed this past January. Nearby, in the Biltmore Village, is the Dickens Festival, a two-day event held on the first weekend in December. The village transforms into a Victorian-era holiday town that holds various events to celebrate the season. For a festive shopping and dining experience, head over to the Grove Arcade and enjoy the suspended light displays and decorations. The seasonal décor will lift your spirits while you check gifts off your holiday shopping list. And finally, check out the Winter lights illumination at the North Carolina Arboretum; there are over a million lights along the open-air walk-through displays! Don’t be a Scrooge, head to Asheville


Winni Wanderer | Santa Claus Indiana

Santa Claus, Indiana

Just the name Santa Claus evokes a warm holiday feeling. Roast some chestnuts on an open fire in this Christmasy town which features events throughout the season for families of all ages. Don’t miss the live reindeer exhibits, story time with Santa, parades, cookie decorating, and the lighting of Santa’s tree on December 1st. Some of these events take place at the Santa Claus Christmas store (which is also perfect for picking up some last-minute gifts), and the Santa Museum & Village. Santa Claus is easily a place to create a family tradition or two with all the places to go and things to do during the holiday season.

Have a jolly good time in Santa Claus


Winni Wanderer | St. Augustine, Florida

St. Augustine, Florida

In search of a charming, warm-weather holiday town? Look no further than St. Augustine. As early as mid-November you can find events in the nation’s oldest city. Be dazzled at the Nights of Lights Holiday display and the Lighthouse Illuminations event where you can climb to the top of the lighthouse and take in the spectacular views of the fully decorated grounds and themed trees below. In early December, check out the Christmas Parade along with several performances, concerts, and the Holiday Regatta of Lights – a spectacular boat parade and a light show from the water. Although there won’t be snow in St. Augustine, there will be an abundance of holiday cheer!

Sunscreen and Santa’s sleigh in St. Augustine


Winni Wanderer | North Pole, Alaska

North Pole, Alaska

Another aptly named town for a cozy, holiday visit is North Pole, Alaska. The North Pole Winterfest & Holiday Bazaar will delight young and old with fireworks, craft vendors, and seasonal goodies. A visit to the Santa Claus House for a picture with the 43-foot-tall Santa statue, a trip to feed the reindeer, and Alaska-made toys and gifts will have everyone in the family smiling ear-to-ear. And don’t forget to join the Parade of Lights in downtown North Pole. For a more traditional Alaskan wilderness experience, the Chena Lakes Region Area is a place to see Alaskan wildlife and try your hand at ice fishing too! All aboard for North Pole

We hope this inspires you to visit one of these charming towns for the holidays! Is there a town near you that is a delight during the holidays? Let us know at WinniWanderer@winni.com. Hearing from you will make our day!


 

By Staff Contributor

 

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