Seasonal Guides
Fantastic Things to Do in Madison, WI, this Winter
Best Things to Do in Madison, WI During Winter
Winter brings out a different side of Madison; frosted in snow, the city feels easier to explore without summer crowds. With frozen lakes surrounding the city and neighborhoods near the Capitol taking on a quieter rhythm, winter is an ideal time to explore the best things to do in Madison for a memorable getaway.
Seasonal events in Madison are a big draw in Wisconsin during winter. The Frozen Assets Festival, held on Lake Mendota, combines outdoor fun with a playful spirit, featuring an on-ice 5K, pond hockey, curling demonstrations, kite flying, and skating. The Wisconsin Union’s Winter Carnival adds another layer of energy with snow sports, fireworks over the lake, and family-friendly activities. Later in the season, nearby Middleton hosts Bockfest, a popular celebration centered on local beer and winter traditions.
Beyond festivals, Madison’s extensive trail system remains active year-round. Winter transforms familiar routes like the Lakeshore Path, sections of the Capital City State Trail, and the UW Arboretum into peaceful places for snowshoeing, cross-country skiing, or bundled-up walks. These outdoor options complement Madison’s strong lineup of indoor attractions.
Cold weather is the perfect excuse to explore what to do in Madison, WI, indoors. Museums like the Chazen Museum of Art offer free admission and rotating exhibits, while the University of Wisconsin campus provides lectures, performances, and galleries open to the public. Dining also shines in winter, with restaurants leaning into comforting seasonal menus and craft cocktails, many of which are located within easy walking distance of downtown.
A Cozy Stay at a Bed and Breakfast in Madison, WI
Choosing a Bed and Breakfast in Madison, WI, that visitors trust adds warmth to a winter escape. The Buckingham Inn offers a welcoming home base just minutes from downtown, set in a charming residential neighborhood with easy access to Madison events and attractions. After a day exploring places to go in Wisconsin during winter, returning to comfortable common spaces and a peaceful guest suite makes the experience feel complete.
Winter mornings begin with a homemade breakfast before heading out to explore more of Madison’s seasonal charm. Whether visiting for a weekend or a midweek getaway, winter in Wisconsin reveals a version of Madison that feels personal, inviting, and worth exploring time and again.
Find the Best Winter Weekend Getaway in the Midwest
Best Weekend Getaway in the Midwest This Winter
Winter is the perfect season to slow down, reconnect, and enjoy a change of scenery, and there is no better place to do that than Galena, Illinois. If you are searching for the best weekend getaway in the Midwest, this historic town delivers a memorable mix of seasonal charm, outdoor experiences, and elevated comfort that feels special from the moment you arrive.
Galena shines during winter. Snow-dusted hills set the backdrop for outdoor adventures like skiing and snowboarding at Chestnut Mountain Resort, winter hiking through local preserves, and scenic views along the Mississippi River where bald eagles migrate in the colder months. Downtown Galena remains lively year-round, with independent boutiques, cozy wine tasting rooms, and restaurants perfect for lingering dinners after a full day of exploring. Winter also brings a festive feel to Main Street, making every stroll feel intentional and inviting.
Of course, the best weekend getaway in the Midwest is not only about what you do during the day, but it is also about where you stay. After a day spent enjoying all the best things to do in Galena, IL, this winter, returning to a space that feels indulgent and unrushed makes all the difference.
A Luxury Galena Bed and Breakfast Experience
Jail Hill Inn offers a refined take on the classic Galena Bed and Breakfast. Each morning begins with a gourmet, multi-course breakfast featuring freshly roasted coffee, house-made pastries, fruit, and a rotating main dish, all prepared to start your day on the right note. Guests can enjoy breakfast in the dining room or opt for in-suite service at no additional charge.
In the afternoon, unwind with a private wine and appetizer experience delivered directly to your suite. Thoughtfully prepared charcuterie, baked treats, and your choice of wine allow you to relax without ever needing to leave your room. Spacious suites, luxury linens, and quiet evenings create the ideal environment for rest and connection.
With top national rankings and limited winter availability, Jail Hill Inn continues to set the standard for the best weekend getaway in the Midwest. Plan your winter escape now and experience Galena at its most inviting.
Find the Ultimate December Getaway for the Holidays
Best Christmas Getaway in December
A December escape to St. Augustine brings together warm Southern charm, festive energy, and a holiday calendar unlike anywhere else in the country. A St. Augustine Christmas is defined by glowing streets, historic architecture dressed in lights, and seasonal experiences that turn every evening into something special. From the famous St. Augustine Night of Lights to waterfront celebrations, this city offers one of the most memorable holiday trips in the South.
Christmas lights in St. Augustine transform the historic district into a walkable wonderland. Millions of white lights illuminate centuries-old landmarks, the Bridge of Lions, and the bayfront, creating an atmosphere that feels both timeless and joyful. Riding the Night of Lights trolley is an easy way to enjoy the display while learning about the city’s history. Boat cruises across Matanzas Bay provide another perspective, letting you see the lights shimmer across the water.
Beyond the lights, St. Augustine Christmas events fill December with variety. The St. Augustine Christmas parade brings families together downtown with music and festive floats. The Holiday Regatta of Lights highlights decorated boats gliding through the harbor. Candlelit museum tours, holiday markets, concerts at the amphitheater, and seasonal celebrations at the lighthouse all add depth to your stay. There are countless things to do in St. Augustine at Christmas, whether you prefer history, entertainment, or relaxed evenings under the lights.
Where to Stay During Your St. Augustine Christmas Getaway
Choosing the best place to stay in St. Augustine at Christmas time makes all the difference. St. Francis Inn is a historic, centrally located St. Augustine bed and breakfast that allows you to walk to Night of Lights displays, dining, and seasonal events without worrying about parking. Staying close to the historic district gives you the flexibility to enjoy daytime sightseeing and return easily for evening festivities.
This well-appointed bed and breakfast enhances the holiday experience with thoughtful amenities, inviting guest rooms, and warm hospitality. Features like complimentary bikes, private parking, daily breakfast, evening treats, and comfortable gathering spaces create a true home base during December travels. After a full day of St. Augustine Christmas events, it’s a relief to return somewhere calm, welcoming, and close to everything.
If you are planning a December getaway filled with lights, history, and festive Southern charm, a St. Augustine Christmas delivers an experience worth repeating year after year.
Get Out on the Hiking Trails Near Asheville, NC This Winter
Best Hikes Near Asheville for a Winter Adventure
Winter transforms Western North Carolina into a rewarding destination for outdoor exploration, and the best hikes near Asheville take on a whole new character during the colder months. With fewer crowds and crisp mountain air, winter hiking offers a quieter, more immersive way to experience all the wonderful things to do in Western North Carolina. Bare trees reveal long-range views that stay hidden during other seasons, making winter an ideal time for adventure-focused travelers.
Hiking in Asheville, NC during winter delivers more than scenic beauty. Cooler temperatures make longer hikes more comfortable, while frozen waterfalls and frost-lined trails add dramatic detail to familiar routes. Many visitors are surprised by how active and accessible Asheville hikes remain throughout winter, especially on clear days following light snowfall.
Some of the best hikes in North Carolina are found just outside Asheville. DuPont State Recreational Forest remains a favorite for waterfall hikes, including Triple Falls and High Falls, where winter ice formations create striking visuals. Along the Blue Ridge Parkway, trails like Beacon Heights and Graveyard Fields offer panoramic views when conditions allow, making them standout choices for winter adventure. Chimney Rock State Park and Nantahala National Forest also provide rewarding routes for hikers looking to explore western North Carolina beyond the usual summer season.
Where to Stay After Hiking Near Asheville
After a full day on the trails, having a comfortable place to recharge makes all the difference. The Orchard Inn offers one of the most elevated mountain getaways in North Carolina, pairing outdoor access with thoughtful amenities designed for relaxation. Spacious rooms, suites, and private cottages give guests a quiet place to unwind after hiking near Asheville.
The on-site spa and sauna help ease sore muscles, while fireplaces, jetted tubs in select accommodations, and cozy gathering spaces create a welcoming atmosphere during winter evenings. Each morning begins with a gourmet breakfast, setting you up for another day exploring the best hikes near Asheville.
Winter in North Carolina invites travelers to slow down, embrace the season, and experience the mountains from a fresh perspective. With exceptional trails nearby and a relaxing retreat waiting at the end of the day, this is the perfect time to plan your winter adventure.
Head to the New Hampshire Seacoast for a Winter Getaway
Best New Hampshire Getaway on the Seacoast This Winter
Winter has a way of reshaping a New Hampshire getaway into something more intentional. The air feels crisper, days move a bit more slowly, and time together becomes the only thing you’re tending to. On the Seacoast, winter brings glowing storefronts, quieter streets, and an inviting atmosphere that feels especially well-suited for couples looking to reconnect. For a winter couples getaway, historic Exeter offers charm, walkability, and easy access to some of the best places to visit in New Hampshire.
Exeter blends classic New England character with a creative, close-knit community. You’ll find plenty of things to do in Exeter throughout your getaway. Its downtown is filled with locally owned shops, independent bookstores, coffee spots, and an arts scene that feels genuine rather than staged. Winter is an ideal time to explore, with fewer crowds and more opportunities to slow down and enjoy simple pleasures. Exeter’s Seacoast location also makes it a natural home base for nearby winter adventures, from coastal walks to historic Portsmouth excursions.
An Elevated Stay Among New Hampshire Hotels
For many couples, the highlight of a New Hampshire getaway is choosing the right place to stay. Our historic New Hampshire Hotel, located in the heart of downtown Exeter, offers a refined and romantic alternative to traditional New Hampshire hotels. Set inside a beautifully preserved 1809 mansion, the property features eight thoughtfully designed guest rooms, most with fireplaces that invite you to unwind after a winter day outdoors.
Antiques, museum-worthy artwork, private bathrooms, and luxury linens create an atmosphere that feels polished yet comfortable. Personalized concierge service adds ease to every stay, whether arranging transportation, planning a winter day trip, or securing dining reservations. Romantic packages with flowers, sparkling wine, chocolates, or in-room massages elevate this winter couples getaway even further.
Dining is an essential part of the experience, and Ambrose Restaurant delivers one of the most memorable meals on the Seacoast. Seasonal menus, locally sourced ingredients, and a cozy dining room with a glowing fireplace make it easy to enjoy a refined evening without leaving the property.
A winter New Hampshire getaway feels more meaningful when paired with thoughtful hospitality and a setting designed for couples. If you are planning a winter escape filled with romance, walkable charm, and elevated comfort, Exeter is ready to welcome you.
Hit the Snow With These Michigan Snowmobile Trails!
Best Michigan Snowmobile Trails for Winter Getaways
Winter in the Midwest delivers something special, and nowhere is that more obvious than across Michigan snowmobile trails. When snowfall settles in, thousands of miles of groomed routes connect forests, frozen lakes, and welcoming towns, creating unforgettable Michigan winter getaways for riders of every experience level.
Snowmobile trails in Michigan stretch from the Upper Peninsula to the Lower Peninsula, offering variety that keeps each ride fresh. Riders can cruise wide-open paths, wind through wooded corridors, and stop in small towns where winter hospitality shines. Whether you are chasing adrenaline or planning a relaxed winter weekend, Michigan in winter delivers consistent conditions and scenic rewards.
Upper Michigan snowmobile trails remain a favorite for serious riders. The Upper Peninsula boasts over 3,000 miles of connected routes, with destinations like Ironwood, Paradise, Marquette, and the Keweenaw Peninsula standing out for reliable snowfall and striking scenery. In the Lower Peninsula, snowmobile trails Michigan visitors love include Gaylord, Cadillac, Clare County, and areas shaped by lake-effect snow. Even southern regions provide solid trail networks perfect for shorter winter escapes.
Snowmobiling pairs naturally with other winter activities in Michigan. Skiing, snowshoeing, fat tire biking, scenic chairlift rides, and winter festivals add depth to your itinerary. From frozen waterfalls to brewery stops and local shops, there is no shortage of things to do in Michigan in the winter beyond the trails.
Where to Stay During Michigan Winter Getaways
After a full day outdoors, comfort matters. Michigan Bed and Breakfasts offer warm guest rooms, homemade breakfasts, and thoughtful hospitality that make winter travel feel personal. These locally owned inns are often located near trail systems, dining, and seasonal attractions, making them ideal home bases for snowmobile-focused trips.
Michigan winter getaways combine adventure with ease. With expansive trail networks, diverse winter activities, and inviting places to stay, Michigan snowmobile trails continue to define Midwest winter travel. Plan your winter escape, explore the trails, and enjoy everything Michigan has to offer this season.
How to Enjoy Your Weekend Escape to the San Juans
Best Things to Do in the San Juan Islands This Winter
Winter is an inviting time to slow down and explore the best things to do in the San Juan Islands, especially if you are planning a coastal weekend escape. With fewer visitors, peaceful scenery, and a relaxed pace, winter in the San Juan Islands offers a different and deeply rewarding experience. The islands benefit from a rainshadow effect, which often brings drier weather than surrounding areas, making it easy to enjoy both outdoor adventures and cozy indoor moments.
Friday Harbor is the heart of winter activity on San Juan Island. Spend time browsing local boutiques, independent bookstores, and galleries, or warm up with coffee at a nearby café. The Whale Museum is a favorite winter stop, offering engaging exhibits about the orcas and marine life of the Salish Sea. Art lovers will also enjoy the San Juan Island Museum of Art and the many small galleries scattered throughout town.
Outdoor exploration remains one of the most popular things to do in the San Juan Islands in winter. Forest trails and shoreline paths take on a quieter feel this time of year, creating an ideal setting for hiking, beach walks, and fresh island air. After a day outside, unwind with a craft beer at San Juan Island Brewing or enjoy a relaxed afternoon with a book at Griffin Bay Bookstore.
Cozy Friday Harbor Lodging for a Winter Weekend
After exploring the best things to do in the San Juan Islands, returning to welcoming Friday Harbor lodging makes the experience even better. This well-appointed bed and breakfast in Friday Harbor offers comfortable guest rooms, thoughtful amenities, and inviting spaces to relax after a cool coastal day. Many properties also offer private suites and cottages, perfect for a peaceful winter weekend getaway.
Winter is also the perfect season for a little indulgence. Booking a spa day, enjoying a leisurely meal at one of Friday Harbor’s top restaurants, or simply relaxing by the fire are all part of the experience. With concierge services available to help plan activities, dining, and transportation, your winter visit feels effortless from start to finish.
If you are looking for a refreshing coastal escape, winter in the San Juan Islands delivers. From outdoor exploration to dining, shopping, and comfortable Friday Harbor lodging, there is no shortage of memorable ways to spend a winter weekend. Book your stay and experience it for yourself.
How to Plan Your Winter Getaway at our Luxury Cabins in Washington
Best Luxury Cabin Getaway for Winter in the Gorge
Winter in the Columbia River Gorge is the perfect excuse to slow down and plan a luxury cabin getaway designed for comfort, connection, and adventure. As the season settles in, snow dusts the mountain peaks, the pace of life eases, and the Gorge transforms into one of the most rewarding winter destinations in the Pacific Northwest.
A winter luxury cabin getaway offers the best of both worlds. Outdoor enthusiasts can enjoy skiing and snowboarding on Mount Hood, explore scenic trails with snowshoes, or seek out iconic waterfalls framed by winter light. Many of the things to do in the Columbia River Gorge remain accessible throughout the season, just with a quieter, more intimate feel that makes winter travel even more magical.
After a day spent exploring, returning to a private cabin changes the entire experience. Warm fireplaces, generous soaking tubs, and thoughtfully designed interiors create an inviting place to unwind and truly relax. Winter is when our luxury cabins near Hood River shine, offering an atmosphere that encourages lingering mornings, unhurried evenings, and time well spent together.
A Cozy Retreat Designed for Winter Getaways
Our cabins in the Columbia River Gorge are ideally positioned for winter travelers who want easy access to Mount Hood, Hood River, and the surrounding landscape without sacrificing comfort or a personalized touch. Luxury amenities elevate each stay, while the privacy of a standalone cabin adds a sense of exclusivity that hotels simply cannot match.
Even if you choose to spend a day staying in, the experience feels indulgent. Curl up by the fire, soak away the chill, or enjoy the peaceful setting that winter brings to the Gorge. These moments are what define a true luxury cabin getaway.
Conveniently located within reach of Portland and Seattle, the Columbia River Gorge feels worlds away once you arrive. Winter travel here invites you to disconnect from busy schedules and reconnect with what matters most.
Plan Ahead for the Epic Autumn Glory Festival in Maryland
Best Autumn Glory Festival Romantic Getaway Guide
The Autumn Glory Festival is one of the most anticipated Deep Creek Lake events, offering a distinctive way to experience fall in Maryland. Held each fall, this five-day celebration brings together seasonal traditions, local culture, and the vibrant colors of a classic Maryland autumn. For couples planning a romantic getaway, the festival provides a well-rounded mix of activities set against the backdrop of peak foliage.
The festival schedule features a variety of experiences that highlight the region’s character. The Autumn Glory Grand Parade in downtown Oakland is a central event, with marching bands, floats, and local vendors creating a lively atmosphere. Throughout the week, visitors can explore the artisan markets at Mt. Fresh Pavilion, where locally made goods, seasonal produce, and handcrafted items are available.
Scenic driving tours are among the most popular ways to enjoy fall in Maryland during the festival. These self-guided routes wind through Garrett County, passing landmarks such as Swallow Falls State Park and the Deep Creek Lake Discovery Center. The Turkey Trail adds a culinary element, with local restaurants offering traditional meals that reflect the area’s agricultural heritage.
Beyond the festival, there are additional things to do in Deep Creek during the fall season. Activities include visiting antique and craft shows, navigating a corn maze at Cove Run Farm, and booking a guided horseback ride through the surrounding forest. Outdoor options such as kayaking, biking, and exploring nearby parks extend the experience beyond scheduled events.
Boutique Hotels at Deep Creek Lake
Where you stay is a big part of your Autumn Glory Festival experience. Lake Pointe Inn offers a boutique hotel on Deep Creek Lake, providing convenient access to festival events while maintaining a quiet, lakefront atmosphere. Guests can relax in thoughtfully designed rooms, enjoy lake views, and take advantage of amenities that support a romantic stay.
With its combination of seasonal events, scenic landscapes, and refined accommodations, the Autumn Glory Festival remains one of the best ways to experience Maryland in October. It is a destination that encourages visitors to explore, unwind, and return year after year. This is a very popular time to visit Deep Creek Lake, so be sure to book your lodging well in advance.