When it comes to finding the best things to do in Chestertown, MD, visitors quickly discover that this historic waterfront town offers far more than a typical day trip. Founded in 1706 along the Chester River, Chestertown combines colonial history, a thriving arts community, waterfront recreation, and exceptional dining, making it one of the best Chesapeake Bay towns to explore on Maryland’s Eastern Shore.
The heart of town is the Chestertown Historic District, a National Historic Landmark District filled with preserved colonial architecture, brick sidewalks, independent boutiques, galleries, and river views. Strolling through downtown is one of the most rewarding things to do on the Eastern Shore, offering a glimpse into centuries of Maryland history while enjoying the town’s welcoming atmosphere.
Outdoor enthusiasts will find plenty of opportunities to experience the Chester River. Kayaking and paddleboarding are popular ways to explore the shoreline, where visitors often spot osprey, herons, and bald eagles. For a deeper connection to the area’s maritime heritage, a sail aboard the Schooner Sultana offers an unforgettable experience on the water.
Visitors can also explore Washington College, one of the nation’s oldest colleges, founded in 1782 with support from George Washington. The picturesque campus adds another layer of history and culture to any visit. Nearby, Chestertown RiverArts showcases the town’s creative spirit through gallery exhibits, artist studios, workshops, and community events.
Food lovers will appreciate the variety of restaurants, bakeries, and cafés throughout town. Many feature fresh seafood and locally sourced ingredients that reflect the flavors of the Eastern Shore, Maryland region. A visit to the award-winning Chestertown Farmers Market is another excellent way to experience local culture while shopping for produce, seafood, baked goods, and artisan products.
After a day spent exploring the best things to do in Chestertown, MD, retreat to the Inn at Huntingfield Creek, a welcoming bed and breakfast in Maryland located less than 25 minutes from downtown. Situated on 70 waterfront acres, the property offers comfortable accommodations, peaceful surroundings, and authentic Chesapeake hospitality.
Guests can relax with sunset views, stroll the grounds, or unwind with homemade salted chocolate chip cookies before settling into thoughtfully appointed guest rooms featuring king-size beds and fine linens. Each morning begins with a full country breakfast prepared with fresh ingredients and homemade favorites. Whether you’re planning a romantic escape or a best coast getaway exploring Maryland coastal towns, the Inn at Huntingfield Creek provides the perfect home base. Book your stay today.
Winter reveals a quieter, more rewarding side of travel, and the best things to do in New England during the colder months go far beyond skiing alone. Snowy villages, cultural attractions, and outdoor experiences create the perfect backdrop for winter weekend getaways in Vermont. From scenic back roads to lively small towns, this season invites travelers to slow down and explore.
Southern Vermont is an excellent place to experience Northeast winter vacations, especially around Brattleboro. Located near the borders of New Hampshire and Massachusetts, this town offers easy access to outdoor recreation while maintaining a strong sense of local character. Days here can be filled with exploration, followed by evenings spent dining, listening to live music, or relaxing indoors.
One of the best places to visit in New England during winter is Mount Snow, just a short drive from Brattleboro. Skiing and snowboarding attract visitors from across the region, but non-skiers will also enjoy tubing, snowshoeing, and scenic gondola rides. Back in town, downtown Brattleboro provides a more relaxed pace with bookstores, galleries, and locally owned shops.
Outdoor enthusiasts will appreciate the Retreat Trails, a wooded network just minutes from downtown, ideal for snowshoeing or cross-country skiing. For a unique local tradition, the Harris Hill Ski Jump hosts one of the longest-running ski jumping events in the country, drawing spectators each winter. Nearby villages like Chester add even more charm, offering historic architecture and inviting lunch spots within easy driving distance.
Choosing the right lodging makes winter travel more enjoyable, especially for couples and adults seeking comfort and convenience. Boutique hotels in Brattleboro, VT, place guests close to the best things to do in New England while offering a more personal experience. The Inn on Putney Road offers welcoming guest rooms, a satisfying breakfast each morning, and a location that lets visitors spend the crisp winter days outside and warm, cozy evenings by the fire.
Whether you are planning a short winter escape or a more extended seasonal stay, Brattleboro offers a thoughtful mix of adventure, culture, and relaxation. Winter is an ideal time to discover the best things to do in New England and create a getaway worth repeating.
Few experiences offer a closer look at Pennsylvania Dutch Country than Amish buggy rides through the countryside of Lancaster County. The steady rhythm of horse hooves, the peaceful farmland views, and the slower pace create a memorable way to experience one of the nation’s most distinctive cultural regions. For families visiting Amish Country, a buggy ride provides a respectful introduction to Amish traditions and daily life.
While Amish buggy rides are a highlight of any visit, Lancaster County offers much more to explore. Visitors can spend time browsing local farmers’ markets, discovering covered bridges, shopping for handmade quilts, and enjoying traditional Pennsylvania Dutch foods. These experiences make it easy to build a family getaway filled with authentic local culture.
Several trusted operators offer Amish buggy rides Lancaster PA visitors consistently enjoy. Aaron & Jessica’s Buggy Rides in Bird-in-Hand features a variety of tours that travel through working farmland and residential Amish communities. Their popular Amish Country and Cookie Tour includes scenic countryside views and a stop at an Amish farm. Guests seeking a deeper experience can choose longer tours that include farm visits, roadside stands, quilt shops, and opportunities to learn more about Amish traditions.
Abe’s Buggy Rides is another popular choice for Amish country tours in Lancaster County. Tour lengths range from brief introductory rides to extended experiences that explore more of the surrounding countryside. Longer routes may include views of Amish schoolhouses, local bake shops, and expansive farmland that showcases the agricultural heritage of the region.
After spending the day enjoying Amish tours and exploring Lancaster County, return to Verdant View, one of the most welcoming farms in Lancaster PA. Unlike a traditional hotel, our family-focused Bed and Breakfast allows guests to experience life on a working farm.
Children can participate in hands-on activities such as feeding animals, gathering eggs, and learning about daily farm operations. These experiences create lasting memories while offering a meaningful connection to the agricultural traditions that define the area.
Breakfast is another highlight of the stay. Guests share a meal with farm staff, hear stories about the property, and gain additional insight into the surrounding Amish community. Combined with comfortable accommodations and genuine hospitality, Verdant View provides an ideal home base for families exploring the best things to do in Lancaster County and the beauty of Pennsylvania Dutch Country.
Whether you choose a short ride through the countryside or a more immersive Amish country tour, Amish buggy rides remain one of the best ways to experience the traditions, landscapes, and family-friendly attractions that make Lancaster County such a popular destination. Book your stay at Verdant View and start planning your next family getaway today.
When it comes to unforgettable things to do in Pennsylvania for couples, Mercer County is the full package with charming small towns, unique stops, and luxury indulgence. Whether you are planning Pennsylvania getaways for couples from Cleveland, Pittsburgh, or beyond, this corner of Western PA delivers meaningful experiences designed for time together.
Start your itinerary with the Mercer County Wine, Brew, and Spirits Trail, a self-guided tasting journey through scenic small towns. From rustic wineries and lakeside cellars to craft breweries perched above waterfalls, each stop offers handcrafted drinks and welcoming hospitality. Couples can spend an afternoon sampling local vintages at Gatehouse Winery, enjoy waterfront views at Dockside Cellars, or sip German-inspired brews at Cobblehaus Brewing Co. near Springfield Falls. For those who love variety, Nova Cellars, Brew 32 Craft Brewery, and Scallywag Distilling share a lively tasting space.
Downtown Sharon adds even more personality to your romantic getaway. Browse The Winner’s multi-level shopping experience, explore the chocolate displays at Daffin’s Candies, or catch live entertainment at ACTS Performing Arts Center or Apollo Maennerchor. Outdoor enthusiasts will appreciate nearby parks like Buhl Park and Maurice K. Goddard State Park, where hiking trails, lake views, kayaking, and golf create active options for couples.
A highlight of any Pennsylvania romantic getaway is a stay at Buhl Mansion Guesthouse & Spa. This 1890s-era castle in Sharon welcomes guests with Champagne upon arrival and elegantly appointed suites featuring fireplaces and whirlpool tubs. It’s by far one of the best boutique hotels in Sharon! For couples seeking elevated relaxation, the on-site spa offers massages and treatments designed for two.
Each morning, enjoy a made-to-order breakfast in the sunlit dining room or delivered to your suite. In the evening, unwind with champagne, chocolate-covered strawberries, or a quiet stroll through the manicured grounds. When searching for romantic getaways in Pennsylvania that combine luxury lodging with curated experiences, Buhl Mansion stands out as both your home base and a destination in its own right. Plan your stay and discover why these are truly the best things to do in Pennsylvania for couples.
Vicksburg is a destination that showcases history, culture, and Southern charm, making it an appealing choice for couples planning a relaxed getaway. While many visitors come for the renowned Vicksburg Military Park, they quickly discover that there are countless other things to do in Vicksburg, MS, that create a well-rounded and memorable stay.
Set high above the Mississippi River, Vicksburg’s historic neighborhoods offer elegant architecture shaped by centuries of history. Walking these streets together is one of the most rewarding ways to experience the city. The Heritage Walking Tour Map provides an easy route through areas influenced by the Vicksburg Battlefield, where Victorian, Italianate, and Greek Revival homes highlight the city’s past. Touring historic homes like the McRaven House adds even more depth to the experience.
Downtown Vicksburg offers a lively mix of dining, shopping, and entertainment that suits couples looking to explore. Browse local galleries and boutiques, then enjoy lunch at popular cafes such as Walnut Hills or Main Street Market Cafe. In the evening, dinner spots like Restaurant Anchuca or Rusty’s River Front Grill provide inviting settings for a night out.
A visit to Vicksburg National Military Park is essential for first-time visitors and returning guests alike. Scenic driving routes, monuments, and walking trails offer thoughtful ways to explore together. Afterward, head to the Mississippi River for a different perspective. Guided sightseeing or fishing tours highlight the river’s role in the city’s story.
Choosing the right lodging enhances every couple’s getaway. Staying at a Bed and Breakfast in Vicksburg places your accommodations at the heart of the experience. Oak Hall offers spacious private guest rooms and suites inside a beautifully restored Mission Revival mansion, just minutes from downtown and major Vicksburg Mississippi attractions.
Evenings are perfect for unwinding on the porches or enjoying sunset cocktails at 10 South Rooftop Bar & Grill, known for its Mississippi River views. With history, walkable attractions, and welcoming hospitality, Vicksburg offers couples an inviting Southern escape filled with memorable experiences.
For travelers planning an unforgettable island adventure, understanding the best time to see orcas in the San Juan Islands makes all the difference. These waters are part of the Salish Sea, one of the most reliable regions in the Pacific Northwest for orca whale watching. While whales can appear year-round, spring and summer consistently offer the most rewarding sightings.
San Juan Island Whale watching season typically begins in April and extends through October, with peak activity from May through September. During spring, salmon begin returning to the region, drawing Southern Resident orcas closer to San Juan Island. As summer arrives, sightings become even more frequent, and the calm seas create ideal conditions for both boat tours and shore-based viewing. This is why many travelers consider this period the best time to see orcas near Seattle and across Washington.
What makes whale watching in the San Juan Islands especially exciting is the variety of species you may encounter. In addition to Southern Resident pods, Bigg’s killer whales regularly pass through, offering a different and thrilling style of orca whale watching. Humpback, gray, and minke whales are also common during peak months, adding to the sense of adventure on the water.
Visitors can experience whales in several ways. Whale watching tours departing from Friday Harbor are led by knowledgeable guides who track whale activity daily and share insights into behavior and conservation. For those who prefer staying on land, Lime Kiln Point State Park is widely considered one of the best places to see orcas in Washington, with frequent shoreline sightings during the summer months.
After a day filled with salt air and unforgettable encounters, having the right place to stay enhances the entire experience. Our Boutique Hotel in Friday Harbor offers refined island accommodations just steps from the ferry and downtown. Guests enjoy beautifully designed rooms, personalized service, and thoughtful amenities like breakfast delivered to your door each morning. With easy access to whale watching tours and other things to do on San Juan Island, it’s an ideal home base for planning your spring or summer escape.
From kayaking and hiking to spotting orcas offshore, San Juan Island delivers an adventure that feels both wild and welcoming. Plan your visit during the best time to see orcas, and experience why this destination continues to stand out as one of the best places to see orcas anywhere in Washington.
Whale migration on the Oregon Coast is one of the most exciting wildlife experiences available to travelers who enjoy scenic views and outdoor adventure. Unlike many destinations that require boat tours, Oregon Coast whale watching often happens right from shore, allowing visitors to spot massive marine mammals while exploring beaches, headlands, and coastal viewpoints.
Multiple whale species travel along the Oregon Coast throughout the year, making sightings possible in every season. Gray whale migration draws the largest numbers, with peak movement south from mid-December through mid-January and a return migration from late March through May. Summer and early fall extend the Oregon Coast whale-watching season as resident gray whales feed offshore, while humpback whale migration peaks in late summer and early fall. Orcas and other species make occasional appearances, adding to the excitement.
The southern Oregon Coast offers especially strong viewing opportunities thanks to elevated viewpoints and accessible shoreline. Areas near Bandon offer dramatic coastal scenery that suits travelers looking to balance adventure with relaxation. Morning hours are often ideal for spotting spouts, as calmer waters and lighter winds make whale activity easier to see.
Some of the best land-based whale watching near Bandon can be found along the Oregon Whale Trail. Battle Rock Wayside Scenic Viewpoint offers elevated views that help visitors scan offshore waters. Cape Arago is another popular location, particularly during winter and spring gray whale migration, while Face Rock Wayside Scenic Viewpoint allows whale watching directly from the shoreline. Bringing binoculars improves your chances of spotting spouts, flukes, and surface activity.
Staying nearby makes it easier to enjoy whale migration on the Oregon Coast. Choosing accommodations close to the shoreline allows travelers to take advantage of changing conditions and spontaneous sightings. Hotels in Bandon place guests near several official viewing locations while offering a comfortable retreat after cool, breezy days outdoors.
Inn at Face Rock is in an ideal location to take in the excitement, but then retreat in the evenings. Well-appointed guest rooms, an indoor heated pool and hot tub, and a complimentary breakfast buffet each morning round out the offerings. Whether you’re tracking gray whale migration, hoping to glimpse humpback whales, or simply enjoying time along the coast, whale migration on the Oregon Coast offers a memorable adventure built around natural beauty and discovery.
When couples are searching for weekend trips from Cleveland that feel special without requiring long travel days, winter is the perfect season to stay close and relax nearby. Just 1.5 hours southeast of the city, Sharon, Pennsylvania, and the surrounding Mercer County area offer an easy winter escape where snow-covered scenery, quiet streets, and thoughtful experiences create space for connection.
Winter weekend trips from Cleveland are especially appealing for couples celebrating anniversaries or simply looking for time together. Less time on the road means more time enjoying cozy mornings, relaxed afternoons, and evenings designed around comfort and conversation. Mercer County, PA, delivers all of that while still feeling removed from everyday routines.
Downtown Sharon invites leisurely walks past historic buildings, local shops, and seasonal events that bring warmth to winter weekends. Short drives lead to nearby towns like Mercer and Grove City, where antique stores, cafes, and historic attractions add variety without feeling rushed. Local wineries, including The Property by Nova Destinations, remain a favorite stop for couples seeking tastings and relaxed date nights.
A stay at Buhl Mansion Guesthouse and Spa turns weekend trips from Cleveland into a complete couples getaway. The historic castle-style architecture sets the tone from the moment you arrive, while spacious guest suites offer fireplaces, elegant bathrooms, and the privacy couples appreciate in winter. Each room blends character with comfort, making it easy to unwind after a day exploring the region.
Dining is another highlight of winter trips to Mercer County. Cozy restaurants and locally owned spots focus on quality and atmosphere, with Stonewall’s Tavern at Tara being a favorite for romantic dinners year-round. Seasonal performances and community events add another layer to the experience, especially during colder months.
Of course, many couples choose to spend much of their stay at the mansion itself. The on-site spa offers indulgent packages designed for two, ranging from full-day experiences to shorter massage-focused escapes. With spa lunches, champagne, and thoughtful details, it is easy to turn a winter weekend into a meaningful celebration.
For couples seeking anniversary destinations or memorable winter weekend trips from Cleveland, this romantic Bed and Breakfast in Pennsylvania makes a short drive feel truly special.
Winter is an ideal season for weekend trips from Pittsburgh, especially for travelers looking to slow down and enjoy meaningful time away from the city. Fewer crowds, cozy settings, and shorter drives make winter weekends perfect for spontaneous escapes. Heading further north into Pennsylvania’s countryside offers an easy change of scenery without the stress of long travel days.
Mercer County stands out as one of the most appealing areas for winter weekend getaways in PA. Quaint towns, scenic country roads, and seasonal activities suit couples and friends alike. Choosing romantic getaways within two hours of Pittsburgh keeps travel flexible, which is especially helpful when winter weather can change plans quickly.
Downtown Sharon provides a welcoming small-town experience with local shops, coffee spots, and casual dining. A visit to the Spa at Buhl Mansion adds a layer of indulgence, with full-service treatments and couples massages that feel especially restorative in winter. For shoppers, Grove City Premium Outlets offer excellent off-season and tax-free deals just a short drive away, making it a favorite stop on weekend trips from Pittsburgh.
Outdoor exploration remains rewarding even in colder months. Winter walks at Buhl Park or along the trails at Maurice K. Goddard State Park offer open views and peaceful surroundings. Many couples also enjoy exploring the Mercer County Wine, Brew, and Spirits Trail, where winter tastings allow more time to talk with staff and enjoy each stop without crowds.
Where you stay can influence the entire experience of your winter getaway. For travelers seeking weekend getaways in PA that feel personal and relaxed, a Bed and Breakfast in PA offers a natural fit. Tara – A Country Inn offers an inviting setting with attentive hospitality, homemade breakfasts, and on-site dining options, eliminating the need to venture far to find an elegant meal.
Spending evenings by the fire, enjoying a nightcap in the lounge, or relaxing in your guest room encourages guests to slow down and reconnect. Winter weekend trips from Pittsburgh are about comfort, simplicity, and quality time, and Mercer County delivers on all three.