Small Town Weekend Getaways

Location:

Woodstock, VT

Highlights:

Woodstock, VT is the perfect destination for active couples, offering year-round outdoor activities and a romantic atmosphere. Nestled in the Green Mountains, this charming town is ideal for a quick weekend getaway with breathtaking scenery and plenty to explore.

We Recommend This For:

Couples looking for adventure, nature lovers, and anyone seeking a romantic retreat surrounded by the beauty of Vermont.

What We Love:

The town's diverse activities for all seasons, whether it's skiing in winter or hiking in summer, and the romantic ambiance that defines Woodstock.

• Winter offers cross-country and downhill skiing, followed by cozy evenings by a log fire in a charming lodge.
• Spring and summer are perfect for hiking, biking, fishing, and rock climbing, with plenty of outdoor activities to keep you active.
• Autumn is a spectacular time for a scenic drive along the Vermont Scenic Byway to see the vibrant fall colors.
• Take to the skies on a romantic hot-air balloon ride, offering breathtaking views of the stunning fall foliage.

Location:

Seabrook Island, SC

Highlights:

Seabrook Island, SC is the perfect beach-side getaway just 30 miles south of Charleston. With pristine white-sand beaches, plenty of activities, and stunning accommodations, this private island offers everything you need for a relaxing and romantic retreat.

We Recommend This For:

Couples, beach lovers, and those looking for an active yet relaxing vacation with scenic beauty and top-tier amenities.

What We Love:

The opportunity to explore Seabrook Island by bike, stroll along the beach at sunset, and enjoy a range of recreational activities like golf, tennis, and horseback riding.

• Relax on over three miles of pristine white-sand beaches, perfect for swimming, sunbathing, and sunset walks.
• Explore the island on bike, with rentals available at Alligator Bike or the Island Bike and Surf Shop.
• Enjoy horseback riding on the beach, a unique and romantic way to take in the stunning ocean views.
• Take an island-hopping boat charter for a scenic exploration of the area’s beautiful coastline.
• Unwind at one of the two large swimming pools or the fitness center, and indulge in shopping and dining at Freshfields Village.

Location:

McMinnville, OR

Highlights:

McMinnville is a delightful town in the heart of Oregon's Willamette Valley, known for its world-class wineries and rich history. Whether you’re a wine enthusiast or simply exploring the area's cultural attractions, McMinnville offers an unforgettable experience.

We Recommend This For:

Wine lovers, foodies, history buffs, and anyone seeking a charming and scenic getaway in Oregon’s premier wine region.

What We Love:

The perfect blend of exceptional wine-tasting experiences, cultural attractions, and charming Victorian accommodations, all within a picturesque historic district.

• Taste local wines with the McMinnville Wine Passport, an entertaining and educational self-guided tour through the historic district.
• Explore the Evergreen Aviation Museum, home to aviation history and the iconic Spruce Goose.
• Discover the Yamhill Valley Heritage Center and immerse yourself in the region's fascinating history.
• Stroll through the thriving arts and culture scene, with galleries, theaters, and charming shops.
• Stay in one of the town’s cozy Victorian B&Bs or boutique hotels, many offering a romantic, historic atmosphere.

Romantic Small Town Weekend Getaways:

Location:

Doylestown, PA

Highlights:

Doylestown, located just 27 miles from Philadelphia, is a charming and unique getaway destination. With a blend of history, outdoor activities, and culinary experiences, this town offers something for everyone on a weekend trip.

We Recommend This For:

History buffs, art lovers, foodies, and outdoor enthusiasts looking for a relaxing yet enriching weekend.

What We Love:

The combination of fascinating historic sites, vibrant art scenes, and delightful food experiences that make Doylestown a standout destination.

• Explore the remarkable Fonthill Castle and Museum, a must-see attraction that showcases unique architecture and history.
• Discover historic landmarks like the Tudor-style Aldie Mansion, the Pearl S. Buck House, and the Mercer Museum.
• Admire Pennsylvania Impressionist art at the James A. Michener Art Museum, a treat for art lovers.
• Sample local produce at the Doylestown Farmer’s Market, or enjoy a brew at the Doylestown Brewery.
• Indulge in a Bucks County Food Tour or a wine-tasting experience for a truly satisfying getaway.
• Enjoy the outdoors with hiking, biking, and rock climbing for a healthy, active experience.

Location:

Lookout Mountain, AL

Highlights:

Lookout Mountain offers a peaceful escape for couples looking to reconnect with nature. Located in northeastern Alabama, this beautiful mountain retreat provides a perfect blend of adventure and tranquility for a romantic weekend getaway.

We Recommend This For:

Couples, outdoor lovers, and anyone seeking a quiet, scenic getaway with a variety of outdoor activities.

What We Love:

The chance to immerse yourself in nature, from hiking and biking to kayaking and rock climbing, all while surrounded by breathtaking views.

• Stay in a romantic log cabin at DeSoto State Park, where you can enjoy cozy evenings and scenic beauty.
• Hike and bike through miles of picturesque trails, or enjoy a relaxing picnic in a beautiful natural setting.
• Experience thrilling outdoor adventures like horseback riding, rock climbing, rappelling, and kayaking.
• Fish in the Little River, known for its great fly fishing opportunities in a serene environment.

Family-friendly Small Town Weekend Getaways:

Location:

San Luis Obispo, CA

Highlights:

San Luis Obispo is one of California's best-kept secrets, offering the perfect mix of food, wine, culture, and outdoor adventure. With over 300 days of sunshine each year, this charming city is ideal for a romantic weekend filled with natural beauty and exciting activities.

We Recommend This For:

Foodies, wine lovers, couples seeking outdoor adventure, and those looking for a combination of relaxation and culture.

What We Love:

The abundance of sunny days, incredible farm-to-fork cuisine, local wines, and a rich cultural scene—all set against a stunning natural backdrop.

• Dine on delicious farm-to-fork cuisine and taste spectacular local wines, making it a foodie paradise.
• Enjoy outdoor activities year-round, including hiking, biking, surfing, zip-lining, and dune riding.
• Take a romantic walk along the beach, soaking in the gorgeous coastal views.
• Experience culture with a visit to the Performing Arts Center, a show at the Great American Melodrama, or the San Luis Obispo Museum of Art.
• Unwind at the amphitheater at Paso Robles with an open-air concert to round off your day.

Location:

Annapolis, MD

Highlights:

Annapolis is a charming retreat known for its cobbled streets, romantic atmosphere, and stunning Chesapeake Bay views. With over 300 floral hanging baskets and historic sites, this town offers couples a perfect mix of romance, history, and coastal beauty.

We Recommend This For:

Couples, history lovers, and anyone seeking a romantic, relaxing weekend by the water.

What We Love:

The romantic atmosphere of the cobblestone streets, historic homes, and the option to cruise the Chesapeake Bay for a truly unforgettable experience.

• Sail away on a Chesapeake Bay cruise aboard the 74-ft Schooner Woodwind, or for extra romance, book an overnight breakfast package.
• Explore well-preserved historic homes and gardens, including the William Packer House with its beautiful two-acre garden and the Charles Carroll House and Gardens.
• Relax in a range of accommodation options, from quaint bed-and-breakfasts to opulent waterfront hotels.
• Stroll along the picturesque cobbled streets, adorned with beautiful floral hanging baskets that enhance the town’s romantic charm.

Unique Small Town Weekend Getaways:

Location:

Aspen, CO

Highlights:

Aspen is not only a world-renowned winter sports destination but also an ideal year-round getaway for couples. Whether you're looking for adventure, relaxation, or romance, Aspen offers unique experiences that make it the perfect place for a proposal, anniversary, or any special occasion.

We Recommend This For:

Couples, adventure seekers, and anyone celebrating a special milestone, offering a mix of romantic activities and breathtaking scenery.

What We Love:

The opportunity to experience unforgettable romantic activities, from soaring over the mountains to enjoying intimate dinners with spectacular views.

• Fly high in a hot air balloon or try paragliding over the stunning Rocky Mountains, often followed by a champagne breakfast.
• Take a gondola ride to the top of Aspen Mountain for a romantic moonlit Friday-night dinner.
• Enjoy summer activities like kayaking and white-water rafting, perfect for couples seeking adventure.
• Relax with a couples massage at one of Aspen’s luxurious spas to unwind after an active day.
• Bond together by taking a cooking lesson, creating lasting memories while learning to prepare delicious dishes.

Location:

Bar Harbor, ME

Highlights:

Bar Harbor is a romantic and scenic destination off the coast of Maine, perfect for couples seeking relaxation and adventure. With its stunning coastal views, outdoor activities, and fresh lobster, Bar Harbor offers everything for an unforgettable getaway.

We Recommend This For:

Couples, nature lovers, and anyone looking for a mix of outdoor exploration and romantic relaxation by the sea.

What We Love:

The breathtaking natural beauty, the chance to experience unique outdoor adventures, and the opportunity to indulge in delicious Maine lobster.

• Hike or cycle along scenic trails with coastal views and the chance to admire luxurious holiday mansions.
• Embark on a romantic whale-watching tour or try your hand at lobster fishing for a true Maine experience.
• Explore Bar Harbor’s museums, galleries, and local shops, offering a glimpse of the town’s vibrant culture.
• Kayak along the stunning coastline or join a rock-climbing tour for an exhilarating adventure.
• Dine on a sublime Maine lobster dinner to end your day in true Bar Harbor style.

Location:

Beaufort, NC

Highlights:

Beaufort is a historic coastal town that has been captivating visitors since 1713. With its rich maritime history, charming streets, and beautiful waterfront, Beaufort offers a perfect mix of relaxation and adventure for couples.

We Recommend This For:

History lovers, maritime enthusiasts, and couples looking for a quiet yet engaging getaway by the sea.

What We Love:

The town's fascinating pirate history, scenic waterfront views, and exciting outdoor activities like wreck diving and dolphin watching.

• Explore Beaufort’s maritime history with a guided walking or biking tour, delving into local legends like Blackbeard and his sunken pirate ship.
• Admire dozens of well-preserved historic homes and enjoy the relaxed atmosphere of the revitalized waterfront.
• Go wreck diving along the coast, discovering the area's underwater history or opt for a dolphin-watching cruise.
• Take a sunset cruise with Lookout Cruises for an unforgettable evening by the water, watching the sun set over the serene harbor.