Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm

Post originally Published December 3, 2023 || Last Updated December 3, 2023

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Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Snowy Mountain Villages Turn Quintessential in Winter


Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm

Snow-covered peaks and icy trails make winter the quintessential season to visit charming mountain villages. The fresh coat of powder transforms these towns, amplifying their old-world allure. Narrow cobblestone streets that bustle with tourists in summer hush under gently falling snowflakes. Steaming mugs of hot cocoa replace chilled glasses of local wine, and roaring fireplaces stand in for breezy patios. When the temperatures drop, the authentic charms of these villages come out in full force.

Vibrant mountain communities like Leavenworth, Washington and Crested Butte, Colorado each offer their own unique brand of character that flourishes amidst winter's chill. Leavenworth represents the quintessential Bavarian mountain village, thanks to its Alpine architecture and seasonal festivals. Visitors can browse the town's myriad German stores, restaurants, and candy shops before strapping on some snowshoes to explore the winter wonderland. Or they can sit fireside with a mug of glühwein at one of Leavenworth's traditional German gasthäuser.

Meanwhile, plunked high in the Colorado Rockies, Crested Butte charms with its historic Victorian storefronts and unpretentious, funky vibe. Once a gritty mining town, Crested Butte has wholeheartedly embraced its role as a winter playground. Snow transforms the rugged mountain terrain into a canvas for outdoor fun. Expert skiers and boarders can tear through double black diamond runs and tree glades at the Crested Butte Mountain Resort, while beginners stick to the wide, groomed slopes. Or try something different, like nighttime skiing under the stars followed by soaking in the resort's rooftop hot tubs. Off the slopes, old mining shacks house quirky art galleries, restaurants, and bars that epitomize Crested Butte's lively spirit.
Part of the allure of these villages stems from their rich histories, apparent in preserved buildings and longtime shops and restaurants. Snowfall provides a poetic juxtaposition that allows the past to shine through peaceful, white scenes draped over the present. Winter also lays the groundwork for beloved traditions and festivals that hearken back generations. Celebrating winter is integral to these communities' identities. Events like Leavenworth's Christkindlmarkt, lighting festivals in mountain towns like Telluride, Colorado, and skijoring - an event involving horseback riding and skiing - in places like McCall, Idaho are beloved institutions. The festivities foster an infectious holiday spirit and camaraderie that pulls in both visitors and locals alike.

What else is in this post?

  1. Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Snowy Mountain Villages Turn Quintessential in Winter
  2. Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Charming Coastal Destinations Offer Off-Season Serenity
  3. Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Historic Small Towns Beam with Holiday Spirit
  4. Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Winter Weather Adds Magic to Lakeside Getaways
  5. Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Mountain Resorts Deliver Winter Wonderlands
  6. Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Small Town Charm Amplified by Snowfall
  7. Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Winter Festivals Give Summer Staples New Life
  8. Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Outdoor Adventures Abound in Cooler Months

Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Charming Coastal Destinations Offer Off-Season Serenity


Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm

When summer fades into fall, hordes of tourists depart from America’s beloved coastal towns. But these quintessential summer destinations still retain their easygoing charm long after beach season ends. The cooler months bring a slower pace, space to roam on vacant beaches, and room at the inn for travelers seeking off-season serenity.

“I like to visit places like Cape May and Bar Harbor once the crowds thin out,” says frequent traveler Amanda L. “You can really immerse yourself in the community and chat with the locals. The shop owners have time to share recommendations, and you can snag a table at popular restaurants without a reservation.”

Without battling summer traffic, you can meander through historic neighborhoods and browse galleries, shops, and eateries at leisure. Nights out listening to live music won’t end with swelling crowds pushing you out the door. And you can wander sandy beaches for seashells and enjoy ocean views all to yourself.
Jim S. frequents coastal New England each fall. “Watching the leaves change while walking the shore is really special,” he shares. “The colors make these quintessential summer towns feel entirely new. I also enjoy bundling up in my fleece to eat lobster rolls on the deck. The chill is refreshing after so much heat.”

Weather varies, but snowfall and holiday decor transform destinations like Newport, Rhode Island into winter wonderlands. Caroling, cocoa, and cozy nights by the fire provide new ways to experience their charms. Or head south to places like Sanibel Island, Florida where temperatures stay mild. Kayaking, biking, and shelling keep you active while peaceful sunsets continue year-round.

Wherever you travel, costs dip along with temperatures. “I’ve gotten great last-minute deals on hotels in Cape Cod during the off-season,” Amanda notes. “It’s so affordable compared to the insane prices all summer. I really maximize my experience without overspending.”

Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Historic Small Towns Beam with Holiday Spirit


Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm

Blanketing historic small towns in twinkling lights and festive decor transforms these destinations into magical wonderlands brimming with holiday spirit. Like something from a snow globe, the adorned storefronts, cobbled lanes, and decorated greens exude quintessential charm. Familiar landmarks glow anew, compelling both locals and visitors to see their community with fresh eyes.

When reminiscing about her recent visit to Woodstock, Vermont in December, Mary B. describes an idyllic New England town radiating Christmas cheer. “Dickensian lampposts lined the streets, each bearing a giant wreath. All the old buildings had garlands in their windows and lights wrapped around the eaves. Woodstock really committed to the holiday aesthetic, but in a classy way that suited the town’s historic vibe.”

Woodstock hosts an annual Wassail Weekend to kick off the Christmas season, featuring carolers, sleigh rides, a yule log ceremony, and fireworks. Like many historic small towns, cherished traditions root the community during the holidays. They foster connections across generations.

The magic stems beyond the aesthetics, according to Susan T., who loves visiting historic Blowing Rock, North Carolina in winter. “Seeing the town covered in snow was breathtakingly beautiful,” she shares. “But what truly shone was the spirit of the people. Strangers said hello to each other on the street. Shopkeepers took time to chat and share town lore. The barista knew everyone’s name.”

Susan notes that winter’s slower pace enables deeper connections to blossom. “Summer crowds move quickly through these towns, but winter invites you to linger. With less hustle, people open up more. I really got a sense of belonging.”

Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Winter Weather Adds Magic to Lakeside Getaways


Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm

The stillness of a frozen lake transforms serene summer destinations into magical winter wonderlands. Glittering snow and ice breathe new life into leisurely lakeside towns, where cooler weather ushers in cozy new adventures. bundled up visitors roam quiet streets that bustled all summer, now insulated in peaceful silence.

“It was like seeing the lake for the first time,” shares Angela R., describing her winter escape to Lake Geneva. “We watched the sunrise glistening on ice that stretched to the horizon. The quiet was profound. I felt present in the beauty of that moment.”

Rather than lament the end of beach season, embrace the gifts winter offers. Tracing snowy paths through silent woods exudes its own majestic charm. The crunch of fresh powder underfoot heightens the senses. Lakeside looked stark and naked in summer reveal their intricate winter beauty.

Winter activities cater to this tranquil pace, centered around comfort and togetherness. Sue K. enjoys ice fishing with her family on Lake Winnipesaukee in wintertime. “Drilling the hole, prepping the bait, and waiting for a bite keeps the kids engaged. Thermos of cocoa in hand, we really connect as a family,” she says.

Cozying up by the fireplace with a book suits Ann B. just fine during her annual winter sojourn to Lake Tahoe. “Going from skiing and crowds in town to the utter serenity of the frozen lake is so refreshing,” Ann says. “I curl up and watch the snow fall through the cabin window, content to just be."

Snow transforms scenic lake towns like Lake Placid into a frozen playground. Glide across mirror-like ice on skates under the glow of dusk. Feel the rush of an exhilarating toboggan ride. Or witness winter’s wonder gliding above snow-covered forests on the Lake Placid ski lift.

Lake Chelan, Washington turns magical when frost kisses its arid cliffs. The ice cave at Frozen Falls intrigues the adventurous, while the heated pool at Sun Cove Lodge beckons after chilled wine tastings.

Winter also showcases lakeside towns’ culinary creativity. Sample Czech, German, and Slovakian influences in the kielbasa, schnitzel and haluski of Lake Geneva’s supper clubs. Sip ice wines and sample frosty craft brews from Lake Tahoe’s local purveyors. Lake Placid’s eateries incorporate fresh regional fare like maple syrup from nearby producers.

Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Mountain Resorts Deliver Winter Wonderlands


Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm

Snow-draped peaks and icy terrain transform mountain resorts into winter wonderlands flush with seasonal activities. While summer offers hiking and biking, winter opens up a range of exhilarating cold weather adventures. Fresh powder blankets rugged landscape, setting the scene for memorable outdoor experiences.

For adventurous spirits, downhill skiing and snowboarding deliver an adrenaline rush. Curt N. makes an annual pilgrimage to Vail, Colorado to experience the resort’s 5,317 skiable acres firsthand. "Plane tickets and lodging feel pricey upfront. But the sheer size of the terrain means I'm never waiting in lift lines. I can tear down runs like Riva Ridge for hours, taking in views of the Rockies all the while."

Snow-covered mountain vistas also create an idyllic backdrop for more low-key pursuits like snowshoeing and cross-country skiing. James R. enjoys this quiet side of mountain resorts. "Gliding along peaceful, wooded trails with my snowshoes provides great exercise without the intensity of downhill. It's incredibly tranquil. I'll pause to watch chickadees flit between snowy pines, feeling totally renewed."

When the body needs a break, mountain resort villages buzz with culture, cuisine, and charm. Snowflake Lake Lodge in McCall, Idaho delights guests with its sloped A-frame buildings encircling a frozen lake. Megan K. loved strolling from her cozy cottage to the main lodge. "The twinkling lights under a blanket of snow made it feel so magical, like I was in my own little snow globe."

Après-ski refueling also delivers comfort. A favorite for many is unwinding by the fire with hot toddies or mulled wine in rustic, timbered restaurants. Resorts like Sun Valley and Aspen tempt with acclaimed fine dining celebrating regional flavors. Foodie Sara C. highlights Pine Creek Cookhouse in Aspen as the ultimate mountain dining experience. "After skiing all morning, we rode a small sleigh to the restaurant for an incredible multi-course meal with wine pairings. It felt like a fairy tale."

When darkness falls, stargazing and night skiing extend the magic. Others prefer burrowing into plush blankets by the fire or soaking in the steamy bubbles of an outdoor hot tub. Most resorts also host live music, craft fairs, ice skating, and other seasonal festivities to delight travelers. The possibilities are endless.

Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Small Town Charm Amplified by Snowfall


Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm

A fresh blanket of snowfall casts everyday scenes in small towns in a magical new light. The white stuff muffles the noises of daily life, bringing a hushed serenity. It cloaks buildings, trees and pathways with picture-perfect coats of powder. In an instant, the familiar transforms into something wonderful and new. For travelers seeking holiday enchantment or a cure for the winter blues, visiting a charming small town after a snowstorm promises magic.

Meg K. spent last Christmas in Woodstock, Vermont shortly after nearly two feet of snow fell over the course of two days. “Everything glittered, it was absolutely breathtaking!” she shares. Though Meg had visited Woodstock in autumn before, this time she saw it reborn under mounds of snow. Icicles dangled from the Village Green’s gazebo like crystal chandeliers. The snow-laden rooftops of covered bridges bowed gracefully under the weight. It was a winter wonderland ripped from the pages of a fairy tale.

Beyond the scenery, Meg was struck by the cozy community atmosphere the weather inspired. “With all the festive decorations lining the snow-covered streets, we all felt like we were living inside a snow globe that had come to life.” Locals emerged to shovel and snowblow walkways, calling out greetings. At the general store, patrons lingered to chat while sipping hot cocoa and coffee. After bundling up for some sledding and snowman building, Meg returned to the inn to find the staff had set out homemade cookies and hot mulled cider. “The steady snowfall brought everyone together indoors. There was so much holiday cheer being shared.”

Over in Holland, Michigan, deep snows annually transform the lakeside village into a winter wonderland. Clad in twinkling lights under full snow loads, the town’s Dutch colonial buildings feel like they were plucked from a Christmas card and brought to life. Locals adorn outdoor spaces with creative snow sculptures that turn heads. When the canals freeze over, ice skating ribbons unfurl offering winter fun. And festive events like Snowfest celebrate the magic snow brings.
Matt A. visited Holland last February to take in the snowy scenes. “The picturesque downtown looked like it was frosted with powdered sugar. I’d seen it during Tulip Time in spring, but winter brought out so much scenic charm.” Matt took pause during an evening stroll down 8th Street. Looking at the snow-topped buildings glowing under streetlights, he felt a deep sense of tranquility wash over him. “The muffled silence, the beauty – it was so serene. The snow made everything feel new again.”

Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Winter Festivals Give Summer Staples New Life


As the chill of winter descends, beloved summer festivals and events get reimagined with creative twists specially suited for the season. By adapting traditions to highlight winter’s gifts, communities delight locals and entice visitors to join the festive fun. From winter carnivals bringing Mardi Gras vibes to snowy climes to frosty new takes on outdoor concerts, festivals add warmth and levity to the shorter, darker days of the year. They also provide new ways to come together and celebrate all that makes your hometown special.

Erin M. eagerly anticipates the annual Snowdown Festival each February in her hometown of Durango, Colorado. “In summer, we have a huge music festival called Bluegrass in the Gulch that takes over the historic downtown. Snowdown puts a winter spin on the event, with live music, street dances, beer, and good grub just like summer. But there’s also a parade, winter games, costume contests, and snow sculptures lining Main Street.”

The winter flair sets Snowdown apart from typical community festivals held in the warmer months. Locals embrace the cold temperatures as part of the fun rather than an inconvenience to tolerate. Costume themes like “Fire and Ice” get creative, incorporating parkas and snow pants along with fun accessories. Snowdown’s popular Polar Plunge into the icy Animas River proves revelers will brave extreme cold for the thrill. “Snowdown brings out Durango’s wild, daring spirit,” says Erin. “It provides a boost of levity to cure the winter blues.”

Over in Ottawa, Canada, the city puts its own spin on summer stars like the tulip with its annual Winterlude festival. Joanne P. attended last year’s edition. “The focal point is the intricate ice sculptures and massive snow playground on the Rideau Canal. But the Canadian Tulip Festival is also highlighted with a display of tulips forced to bloom early indoors. It was incredible to experience summer flowers amidst a snowy winter scene.”

Beyond admiring tulips in January, Joanne was impressed by creative riffs on quintessential summer fun. Snowmen dotted the canal waiting to be decorated by kids and adults alike. An ice dragon boat regatta saw teams in lifejackets paddling vessels carved from crystal clear ice. Snow volleyball courts filled with bundled-up players bumping, setting and spiking despite slippery conditions.

“The activities and ice sculptures were awesome, but my favorite part was the community spirit,” Joanne shares. “Seeing Ottawa residents take so much pride in their wintertime culture was inspiring. Winterlude highlighted everything unique and special about experiencing the city in cold weather.”

Have Your Cake and Eat It Too: 12 Quintessential Summer Towns with Surprising Winter Charm - Outdoor Adventures Abound in Cooler Months


Crisp air and snowy forests call adventurers to lace up their boots and embrace the gifts of the cooler months. While summer offers hiking and paddling under sunny skies, winter opens up options for active travelers willing to bundle up. Fresh powder and chilly temperatures transform landscapes, allowing familiar places to be rediscovered through frozen wonderlands perfect for exploration.

For Matt S., shoulder season is the ideal time to hit the trails. “I love hiking Mt. Monadnock in October when New Hampshire’s leaf peepers have mostly departed. The kaleidoscope of fall foliage views make the workout extra rewarding.” Crisp air and crunch of fallen leaves underfoot heighten the senses too.

Once snow blankets the mountain, Matt eagerly snowshoes to the bare summit. “Everything gets so quiet and peaceful. It’s just me, the wind, and fresh powder. The workout keeps me warm, and the payoff is witnessing breathtaking winter scenes at the top.”

Winter also grants unique access to places typically crowded during warmer months. Emily H. enjoys yurt camping in Rocky Mountain National Park before the summer crowds arrive. “We snowshoe to backcountry sites and spend the night in cozy yurts equipped with wood stoves and bunk beds. Falling asleep under the stars and waking up to mountain views is magical.”

For the truly adventurous, winter camping without yurts takes subzero overnights to the extreme. “Igloo camping on Mount Washington bonded me and my outdoorsy friends for life,” says Shane C. “We hiked up and packed snowblocks to form a shelter, using a saw to carve entrance blocks.” Hunkering beneath mounds of snow as winds whipped to over 100 mph was unforgettable for Shane. “We woke at dawn and boiled coffee on our camp stove, feeling exhilarated to have survived the mountain’s wild winter weather.”

Snow and ice also unlock adventures on waterways that melt and wane in warmer months. “Skating along the frozen Rideau Canal is an iconic Canadian experience visitors shouldn’t miss,” urges Jacques P., who leads tours in Ottawa. Gliding 7.8 kilometers between downtown Ottawa and rural landscapes provides outdoor fun with rich history. “The canal offered a commercial transport route before railroads arrived in the 1850s. Now it hosts one of the world’s largest skating rinks.”

For wilder expeditions, Jacques recommends ice canoeing on the St. Lawrence River outside Montreal. “Paddling across an open expanse of iced-over river channels Canada’s early fur traders. The views are stunning if you can withstand the cold.”

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