Small Towns To Visit During The Winter Months

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Winter travel doesn’t have to mean visiting large towns with big crowds. Small towns have a lot of appeal, especially during the winter months. There’s a lot to do and with so many different choices, you’re bound to be able to have a memorable vacation during this time of year. With the busy season upon us, why don’t you slow down and visit one of these small towns listed below?

Ashland, Wisconsin
This town is so pretty that it’s been featured in quite a few photos. There’s so much to do here, especially for those that want to spend time outdoors. Cooper-Falls State Park is a great place for snowmobilers and skiers to go. There’s a lot to see including frozen waterfalls and gigantic gorges. If you plan on waiting a few months to do some winter traveling, February 16 is a great time to be in Ashland. On this day, Book Across the Bay will be taking place. You can see snowshoers and skiers try to make their way across Lake Superior. What makes this 6-mile trek so unique is that it takes place at night. What this means is that competitors will have to use the light from the stars and lit candles to guide them.

Leavenworth, Washington
Only about 2 ½ hours from Seattle, this town embodies Christmas. It features German-style architecture with numerous timber-framed buildings located throughout it. With the mountains in the backdrop that are covered in snow, you may feel as if you are actually in another country and not in the state of Washington. During the wintertime, you will be pleased to find all sorts of Christmas activities going on. There are Christmas lights everywhere, plus plenty of carolers to get you into the Christmas spirit. If you happen to be in Leavenworth anytime from November 30 to December 16, make sure you check out the Christmas Lighting Festival. There will be over half a million Christmas lights lighting up the town. Christmas lovers can take part in a unique opportunity at the Red-Tail Canyon Farm where they can go on a sleigh ride. Also, check out the Nutcracker Museum. On site there are over 6,000 different nutcrackers with some of them being from ancient Rome. Animal lovers can visit the Leavenworth Reindeer Farm. They can pet and feed these magical creatures. For those that enjoy being outdoors in the chilly weather, they can head over to the Leavenworth Ski Hill. There are opportunities to go snow tubing or skiing.

Ogunquit, Maine
If you weren’t able to make it to Maine for the magnificent fall foliage, head over to Ogunquit during the winter months for a different type of scenery. There are less than 1,000 full-time residents in this town so you can really enjoy a small town feel. From December 7-9, Christmas by the Sea takes place. There are concerts, wine tastings, gallery tours and of course, a tree lighting ceremony with an appearance by Santa Claus. If you are feeling particularly brave, take part in the Ogunquit Ocean Rescue Polar Plunge that will be taking place on the 9th. While the water temperature can best be described as frigid, it does make for a very memorable time. Ogunquit is also known for its beautiful houses. A great way to see them is to head over to the walking path at Marginal Way. It’s only around 1.7 miles long, but provides beautiful views of both the area’s homes and the shoreline.

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Sue Lobo
Sue Lobo is a four-time Condé Nast Traveler Top Travel Specialist (2023, 2024, 2025 & 2026) and Senior Travel Advisor at Atlas Travel Center, one of the most decorated travel agencies in the United States. With more than 35 years of experience in the travel industry, Sue has planned, booked, and personally accompanied trips for thousands of clients — from first-time cruisers to seasoned luxury travelers who have circled the globe multiple times. Sue's areas of deep expertise include ocean and river cruising, European tours, group travel coordination, luxury travel, honeymoon planning, and family vacation design. She is a CLIA-certified cruise specialist and works within an agency that holds IATA and ARC accreditation and maintains an A+ rating from the Better Business Bureau. Over her career, Sue has been involved in more than 30,000 bookings and has personally coordinated over 200 travel groups — from faith-based group cruises and HBCU alumni trips to women's retreats, family reunions, and corporate incentive travel. What sets Sue apart is not just the credentials — it is the firsthand experience behind them. Sue has personally traveled to more than 20 countries across three continents, including Cuba, Egypt, the United Arab Emirates, and throughout Europe. She has sailed on dozens of cruise ships across nearly every major line, walked the river cruise routes she recommends, and eaten at the restaurants she suggests to clients. Her recommendations come from personal experience, not brochures. In addition to advising clients, Sue writes extensively about travel for The Traveler's Atlas blog — covering everything from cruise line comparisons and overtourism trends to destination guides and practical travel tips. Her writing is grounded in the same expertise she brings to every client conversation: honest, specific, and built on decades of real-world travel experience. Sue is based in the United States and available to help travelers plan cruises, European tours, group trips, river cruises, honeymoons, family vacations, and more. To work with Sue, contact Atlas Travel Center at atlastravelweb.com.