Some traditions never go out of style, especially in the Midwest. Wisconsin supper clubs are as much about the ritual as the menu, featuring a cozy evening that starts with conversation, warm lighting, and a well-made Wisconsin old-fashioned. If you’re planning a couples getaway to Wausau, you’ll find the perfect mix of classic dining, arts and culture, and an easy pace that makes it simple to linger a little longer.
Start your day exploring things to do in Wausau, then turn the evening into a fabulous date night at one of the Wisconsin Supper Clubs near Wausau. Catch a live show at the Grand Theater, spend time at the Leigh Yawkey Woodson Art Museum, or step into local history at the Woodson History Center. For a slower stroll, wander the Andrew Warren Historic District, where the preserved architecture sets the scene for an intentional, not rushed, date night. Between Wausau restaurants and the supper club spots just outside town, there’s no shortage of places to eat in Wausau and beyond.
Wisconsin supper clubs took hold in the early to mid twentieth century, built around hospitality, familiarity, and a little bit of ceremony. If you’re wondering what is a supper club, it’s a dining experience packed with nostalgia, including relish trays, prime rib, fish fry, brandy after dinner, and staff who treat you like you’ve been coming for years. Many of the best supper clubs in Wisconsin sit along scenic highways or near water, with cozy booths and menus that lean into steak, seafood, and house-made desserts.
For supper club options near Wausau, Pinewood Supper Club is a local favorite for steaks and prime rib, The Palms Supper Club offers an elevated date-night feel, Sky Club Supper Club is known for classic hospitality and crowd-pleasers like fish fry, and Belvedere Supper Club adds a slightly more modern edge with a dessert list worth saving room for.
After dinner, come back to Stewart Inn, one of the most Unique Hotels in Wausau, WI. Our historic property blends architectural elegance with contemporary comfort, an inviting fit for couples planning a romantic night away. Select suites feature fireplaces for a quiet evening in, and spa-inspired bathrooms make it easy to take your time in the morning. Each day begins with a gourmet multi-course breakfast, prepared in-house and beautifully presented, plus complimentary beverages throughout the day.
When you’re ready to plan, book your couples getaway at Stewart Inn and make the tradition yours.
Bend Breweries are one of the biggest reasons families choose Central Oregon for an easygoing getaway. Known for creativity, variety, and welcoming atmospheres, breweries in Bend, Oregon, make it simple to enjoy outdoor adventure with relaxed dining and local flavor. With mountains, rivers, and trails surrounding the area, families can spend the day exploring and still enjoy an afternoon stop along the Bend Ale Trail.
What sets Bend Breweries apart are the family-friendly options. Outdoor seating, spacious patios, dedicated kids’ menus, and nearby parks create an environment where parents can enjoy a great beer while kids have room to play. From long-established favorites to newer breweries adding fresh styles, the Bend Ale Trail offers more than 30 stops, each with its own personality and appeal.
Popular family-friendly stops include 10 Barrel Brewing, located near Columbia Park, making it easy to combine lunch with playground time. Bend Brewing in the Old Mill District offers grassy outdoor areas and a menu that goes well beyond pub basics. Deschutes Brewery remains a must-visit for families, thanks to its lively atmosphere, approachable food, and history as one of Bend’s original breweries. For something a little different, Worthy Brewing adds a fun twist with its Hopservatory (for nighttime stargazing), while Crux Fermentation Project stands out for its open lawn, welcoming vibe, and easy-drinking beers.
After a day spent exploring Bend Breweries, having a comfortable place to return to makes all the difference. Staying at one of the coziest hotels in Gilchrist, Oregon, allows families to enjoy quick access to Bend while ending the day in a quieter, more relaxed setting. The Historic Gilchrist Waterfront Resort offers space to spread out, cabin-style lodging, and hot tubs with lakefront views.
Cabins and lodging options provide families and groups with flexibility, whether you are traveling with kids or planning a getaway with friends. Common indoor areas invite guests to gather, unwind, and play games. Choosing hotels in Gilchrist, Oregon, as your home base keeps the focus on comfort, convenience, and enjoying everything Central Oregon has to offer.
For families planning a getaway centered around great food, relaxed experiences, and spending time together, this region delivers a trip that feels fun, flexible, and easy to enjoy.
A visit to Driftless Glen Distillery is one of the most distinctive ways to explore Wisconsin distilleries, especially for travelers looking for a unique Midwest getaway. Located along the Baraboo River, this celebrated grain-to-glass distillery has earned national recognition for its craftsmanship, atmosphere, and award-winning spirits. From the moment you arrive, it is clear that Driftless Glen Distillery is a memorable and one-of-a-kind discovery!
Founded in 2012, Driftless Glen has built its reputation on precision and quality. Every bottle, from Driftless Glen Bourbon to rye whiskey, brandy, vodka, and gin, is produced on site using carefully sourced grains. Guided tours offer an inside look at the distillation and barrel aging process, giving visitors a deeper appreciation for what sets this operation apart from other Wisconsin distilleries.
After the tour, the tasting room invites guests to slow down and savor the experience. Tastings highlight the unique character of each spirit, while the full-service restaurant further elevates the visit. Overlooking the Baraboo River, the dining room and outdoor patio create one of the most beautiful settings among restaurants in Baraboo, WI. The menu features hearty steaks, seafood, and thoughtfully crafted dishes designed to pair beautifully with their spirits, making it one of the most talked-about restaurants in Baraboo.
Pairing your distillery visit with a stay at a Baraboo Bed and Breakfast creates a balanced and relaxing getaway. After an afternoon of tastings and dining, returning to a quiet, historic property offers the comfort and calm that travelers appreciate. A well-located inn provides easy access to Driftless Glen Distillery, downtown Baraboo, Devil’s Lake State Park, and other top restaurants in Baraboo, WI.
Guests enjoy spacious common areas, inviting porches, and peaceful evenings that complement the energy of a day spent exploring. Mornings begin with a home-cooked breakfast at the original dining table of the famed Ringling family, giving you a relaxed, historic start before heading out again.
For those seeking a unique Midwest experience built around exceptional spirits, memorable dining, and welcoming hospitality, Driftless Glen Distillery stands out as one of Wisconsin’s most rewarding destinations. And with the Ringling House Bed and Breakfast as your home base, you’ll fall in love with Baraboo on your next visit.
Dining out is a big part of what makes a getaway feel like a getaway. When couples plan romantic trips in Maryland, memorable meals often sit right alongside scenic views and comfortable lodging. Deep Creek Lake restaurants deliver on all fronts, offering everything from fresh seafood and steak dinners to craft cocktails enjoyed with lakefront and mountain backdrops.
After a day spent exploring the area, whether that means browsing antique shops, spending time on the lake, or skiing at Wisp Resort, sitting down to a great meal is the perfect way to unwind. Deep Creek Lake is a four-season destination, and its dining scene reflects that energy. Menus feature locally inspired ingredients, familiar favorites, and creative dishes, giving couples plenty of options for casual lunches or elevated dinners.
Some of the most popular restaurants in Deep Creek Lake, MD, include Pine Lodge Steakhouse, known for its crab cakes and perfectly cooked steaks, and Firewater Kitchen and Bar, a favorite for scratch-made cocktails and lakeside views. Dutch’s at Silver Tree offers a more refined experience with seafood, steaks, and seasonal outdoor dining, while Mountain State Brewing provides a relaxed setting with house-brewed beer, wood-fired pizza, and homemade root beer. Whether you prefer a lively atmosphere or something more intimate, Deep Creek restaurants make it easy to plan each evening around your mood.
Lake Pointe Inn places couples close to the best dining in the area while offering a peaceful retreat to return to afterward. As a small boutique property with secluded suites, this Deep Creek Lake Hotel provides a private, comfortable experience that pairs well with romantic evenings out. Guest rooms feature thoughtful details like fireplaces, jetted tubs, and lake views, creating a space to relax after dinner.
Breakfast is included each morning and prepared fresh on-site, giving you a delicious start to your day before heading out to enjoy more things to do in Deep Creek. An on-site spa adds another layer of indulgence, making it easy to turn a dining-focused trip into a complete romantic escape. If you’re planning a romantic getaway centered around great food, scenic surroundings, and relaxed luxury, Deep Creek Lake restaurants are reason enough to book your stay.
Exploring a historic downtown area is one of the best ways to experience a city’s personality, and Kalamazoo restaurants make that exploration especially rewarding for couples on a Midwest getaway. Known for its walkable streets, cultural attractions, and creative dining scene, Kalamazoo offers memorable meals year-round. From vibrant summer patios to cozy fall and winter dinners, dining out here is both approachable and exciting. There are so many fantastic things to do in Kalamazoo!
One of the highlights of visiting is discovering the variety of downtown Kalamazoo restaurants that locals genuinely love. Principle Food and Drink is a favorite, offering familiar comfort dishes made with locally sourced ingredients and a robust drink menu. For a European-inspired dining experience, Rustica focuses on seasonal flavors and sustainable practices, complemented by a thoughtfully curated wine list.
Sushi fans will enjoy options like Maru Sushi & Grill and Toba Sushi & Grill, both adding fresh variety to the city’s dining landscape. For an evening with cocktails and atmosphere, Dabney & Co. combines expertly crafted drinks, live music, and Southern-inspired small plates, creating a lively yet intimate setting for couples. Casual favorites like The HUB Tavern + Grill and WL Social House round out the scene with crowd-pleasing menus that cater to a wide range of tastes and dietary preferences.
Choosing the right lodging enhances every part of your vacation. Staying at a Boutique Hotel in Kalamazoo, Michigan, places you close to the city’s most popular restaurants while offering a more personal and relaxed stay. With just ten guest rooms, guests enjoy thoughtful hospitality, modern comforts, and a sense of privacy that larger hotels cannot match.
Mornings begin with a freshly prepared breakfast included with your stay, enjoyed in inviting common spaces or on outdoor porches overlooking landscaped gardens. After a day of exploring museums, shops, and downtown dining, returning to a welcoming and character-filled hotel feels like part of the getaway itself. When you are ready to plan your next couples’ escape, book your stay and experience the best Kalamazoo restaurants with comfort and ease.
Lititz restaurants have become a destination in their own right, drawing visitors who appreciate thoughtful food, inviting spaces, and a dining scene that feels both established and fresh. Located in the heart of Amish Country, Restaurants in Lititz, PA, reflect a balance of heritage and creativity, making the town an appealing choice for couples planning a culinary escape.
Walking through downtown, it is easy to understand why places to eat in Lititz play such a central role in the experience. Cafes and bakeries set the tone in the morning, while pubs and chef-driven kitchens take over as the day unfolds. Tomato Pie Cafe is a favorite for breakfast or lunch, especially for espresso drinks and their signature tomato pie. Bulls Head Public House brings British pub character to Lititz PA restaurants, with a fantastic beer list and comforting classics that suit a relaxed afternoon or casual dinner.
For lighter fare or a midday break, Dosie Dough offers freshly made breads, bagels, and wraps that locals rely on. Appalachian Brewing Company adds energy to the lineup with house-brewed beers and elevated pub favorites, while Rooster Street Brewing focuses on quality ingredients and creative preparation, making it a frequent recommendation among Lititz restaurants.
Couples looking for a more polished evening have several strong options. Per Diem, located just outside downtown at Rock Lititz, delivers seasonal menus and a refined dining room that attracts both locals and visitors. The White Swan provides classic American fare in a historic setting, while Kole Chophouse stands out for steakhouse-style dining that feels well-suited for celebrations or date nights. For those willing to venture slightly beyond town, the Brunnerville Hotel and Brickerville House offer comforting meals that continue to earn loyal followings.
Pairing great dining with the right place to stay completes the experience. Historic Smithton Inn is a refined Ephrata Bed and Breakfast that offers couples a welcoming retreat after exploring Lititz restaurants. Dating back to 1763, the Inn blends historic character with modern comfort, elegant rooms, and an inviting wine bar. Its location makes it easy to enjoy restaurants in Lititz, PA, and discover the other great things to do in Lancaster County while having a quiet place to unwind together. Reserve your stay and plan a couples getaway centered around some of the best dining in Amish Country.
Minnesota has earned its reputation as a top destination for beer lovers, offering a mix of historic brewing roots and a constantly evolving craft beer scene. From classic lagers to creative seasonal releases, Minnesota breweries showcase both tradition and innovation, making them an ideal focus for a Midwest weekend getaway.
Across the state, breweries in Minneapolis, Minnesota, and breweries in Duluth, Minnesota, continue to draw attention for their quality and variety. Minneapolis breweries range from well-established names to inventive small-batch producers, while Duluth’s breweries often reflect their North Shore surroundings with bold, refreshing styles. Beyond the cities, local breweries in small towns and scenic regions add even more personality to Minnesota beer culture, giving travelers plenty of reasons to explore beyond the main hubs.
A weekend built around Minnesota beer is easy to plan thanks to the growing number of brewery districts, taproom trails, and seasonal releases that keep menus fresh. Whether you prefer hop-forward IPAs, smooth dark ales, or lighter styles that pair well with food, the best breweries in Minnesota offer something for every palate. And that is, of course, just the start of great things to do in Minnesota.
Choosing the right place to stay makes a brewery-focused getaway even better. Minnesota Bed and Breakfasts offer comfortable accommodations, thoughtful hospitality, and convenient access to local breweries. Many innkeepers are familiar with nearby beer spots and can recommend Minneapolis breweries, Duluth favorites, or hidden gems worth the drive. After a day of tastings, relaxing in a cozy guest room or shared space is the perfect way to unwind.
A Midwest weekend getaway centered on Minnesota breweries combines great beer with memorable places to stay. From urban taprooms to small-town breweries, Minnesota beer continues to impress. When you’re ready to start planning, explore places to stay in Minnesota and build a weekend that balances exceptional brewing with welcoming accommodations.
Exploring Cayuga Lake wineries is one of the most rewarding ways for couples to experience the Finger Lakes together. This northern stretch of Upstate New York is known for cool-climate wines, scenic vineyard views, and tasting rooms that feel welcoming rather than crowded. Focusing your itinerary on the Cayuga Lake Wine Trail is one of the best things to do in the Finger Lakes on your next getaway.
Established in 1983 as the first wine trail in the country, the Cayuga Lake Wine Trail winds through lakeside vineyards, rolling farmland, and charming towns like Trumansburg. Along the route, you will find a thoughtful mix of wineries, cideries, and distilleries, making it easy to spend a full day tasting while discovering one of the best things to do in Upstate NY. Many Cayuga Lake wineries are family-owned, with a strong commitment to sustainable practices and handcrafted wines that reflect the region’s distinct character.
Six Mile Creek Vineyard is one of the oldest Cayuga Lake wineries and a favorite for its range of award-winning wines and spirits. Lucas Vineyards offers sweeping lake views alongside estate-grown wines, sparkling selections, and guest-loved Rieslings. Hosmer Winery brings a sense of heritage to the trail, producing expressive varietals from its long-established vineyards. Thirsty Owl Wine Co. stands out for its expansive tasting room overlooking the lake and a seasonal bistro that pairs local ingredients with estate wines. Cayuga Ridge Estate Winery and Buttonwood Grove Winery round out the experience with welcoming tasting rooms and some of the most scenic overlooks on the trail.
After a day exploring wineries in the Finger Lakes, couples appreciate having a comfortable and inviting place to unwind. Staying near Cayuga Lake allows you to extend your getaway across multiple days, leaving time to explore beyond the tasting rooms. From peaceful mornings to unhurried evenings, a well-located inn enhances the entire experience.
Whether you are planning your first visit or returning to discover new favorites, Cayuga Lake wineries offer a memorable couples getaway filled with great wine, beautiful views, and the relaxed charm that defines the Finger Lakes. The Inn at Gothic Eves is a fantastic boutique hotel & spa in the Finger Lakes to make your home base.
Dining out is one of the most memorable parts of a couple’s getaway, and Madison delivers an impressive mix of creativity, comfort, and locally driven menus. From James Beard-recognized chefs to neighborhood favorites, the restaurants in Madison continue to raise the bar for Midwest dining. Whether you are planning a romantic night out or building an entire trip around food, these places to eat in Madison are worth reserving ahead of time.
One thing that sets Madison, WI, restaurants apart is their deep connection to local farms and producers. Seasonal menus highlight Wisconsin cheeses, fresh produce, and thoughtfully sourced proteins, creating meals that feel rooted in the region. Many of the best restaurants in Madison focus on small plates, shareable dishes, and intimate dining rooms, making them especially appealing for couples.
The neighborhoods surrounding Capitol Square are packed with standout dining options. Lallande offers beautifully crafted French-inspired plates in a cozy setting, while The Harvey House reimagines the classic supper club experience with a modern twist. Gates & Brovi blends Italian influences with Wisconsin traditions, and Heritage Tavern showcases a farm-focused menu led by a James Beard-nominated chef.
For a classic date night, Lombardino’s remains a favorite for Italian comfort dishes, while Sardine delivers lakeside dining with French flair. Eno Vino pairs panoramic views with creative small plates, making it a popular choice for couples celebrating a special occasion. From new restaurants in Madison, WI, to long-standing icons like the Tornado Club Steak House, the city offers plenty of ways to dine well together.
After enjoying the best restaurants in Madison, returning to a comfortable and welcoming place to stay matters just as much. Choosing a charming Bed and Breakfast in Madison, WI, offers a quieter, more personal experience than staying in a large hotel. Staying at a locally owned inn means starting each morning with a homemade breakfast and insider dining recommendations tailored to your plans. It is the perfect complement to a couple’s getaway built around great food, thoughtful hospitality, and time well spent together.