7 Picturesque Towns in New England for a Weekend Retreat in 2024
In New England's small towns, leaf-peeping visitors bring millions of dollars annually in fall alone. As the leaves turn fiery hues and the coastal air crisps, consider retreating to the beautiful towns of New England. The wide variety of tree species, like sugar maples, birches, and oaks, give the area its iconic foliage scene. As a result, this region has become the beating heart of US fall escapes, with towns like Kennebunkport and Stowe epitomizing autumn flair. Besides its autumnal charm, New England also invites flocks of people to ski and snowboard in winter and in spring and summer to take in the coastal beauty and outdoor adventures. In other words, this magnificent region of the United States is the place to be any time of year.
Accommodations such as the grand Woodstock Inn and Resort or the historic Kennebunkport Inn offer more than just a place to rest—they provide a portal to the essence of New England, complete with modern comforts and timeless elegance. Join us as we uncover the quiet allure of New England’s most picturesque towns, each waiting to offer its own version of refuge and enchantment in 2024, making every moment a precious memory in the making.
Lenox, Massachusetts
Lenox, in the heart of the Berkshires, is renowned for its stunning Gilded Age mansions, which have turned into cultural hubs. One of the crown jewels is The Mount, the opulent former home of Pulitzer Prize-winning author Edith Wharton, which now hosts a variety of literary lectures and art exhibits. Nearby, the sounds of the Boston Symphony Orchestra resonate through the air at Tanglewood, their summer residence, providing music lovers with unforgettable live performances in a stunning outdoor setting. For those intrigued by the more mysterious aspects of history, the Ventfort Hall Gilded Age Mansion & Museum not only offers tours of its lavish rooms but also hosts ghost-themed tours for the adventurous.
For accommodations, visitors should consider The Playhouse, a historic estate that once hosted figures such as President McKinley and Nikola Tesla. This choice offers a direct connection to the grandeur that once defined Lenox, complemented by modern comforts. Alternatively, the soon-to-reopen Blantyre adds a touch of luxury with its historical ambiance and upscale services, making it an ideal base for those wishing to indulge in a plush retreat. Culinary delights await at Alta Restaurant, where the menu is inspired by Mediterranean flavors, providing a perfect end to a day of cultural exploration and scenic enjoyment.
Newport, Rhode Island
Newport is known for its rich maritime history and the opulent Gilded Age mansions that line Bellevue Avenue. Each mansion, many of which now serve as museums, offers a glimpse into the extravagant lifestyles of America’s elite from the late 19th century. The most illustrious among them, The Breakers, built in 1895, stands as a testament to Renaissance splendor, transporting visitors to an era of unmatched luxury and grandeur. The town’s dedication to preserving its heritage extends beyond these grand homes to the Museum of Newport Irish History, which celebrates the Irish immigrants' significant contributions to Newport's development. For a touch of nature and history combined, Fort Adams State Park offers panoramic views across Newport Harbor and Narragansett Bay, making it a perfect spot for sightseeing and reflection.
Accommodation in Newport caters to a variety of tastes and preferences, ranging from the historic charm of The Chanler at Cliff Walk, which offers direct access to the scenic shore path, to the more contemporary comforts of the Newport Harbor Hotel & Marina, located directly on the bustling waterfront. This diversity ensures that every visitor can find a perfect spot to relax after a day spent exploring the architectural marvels, cultural exhibits at the Newport Art Museum, or engaging in the local sailing and tennis scenes. The International Tennis Hall of Fame, another must-visit, not only provides insights into the sport's history but also invites visitors to partake in the annual Hall of Fame Open tournament.
Camden, Maine
Camden, the "Jewel of the Coast," is perfectly positioned between the mountains and the ocean on Penobscot Bay. Visitors can explore the scenic Mt. Battie Trailhead and the expansive Camden Hills State Park, which offer stunning views of the surrounding landscapes and ample opportunities for hiking and photography. Camden's vibrant downtown district further enhances its appeal, featuring a variety of waterfront dining options, unique boutiques, and the historic Opera House, where live performances captivate both locals and tourists. For those interested in local history, a stroll through the High Street Historic District showcases charming 19th-century homes and some of the oldest continually operating businesses like the Smiling Cow gift shop.
For those seeking a historical experience, the Hawthorn Inn offers a cozy stay in a Victorian mansion dating back to 1894, conveniently located near both the downtown area and the serene Camden Harbor. This inn provides a perfect base for attending local events such as the Camden Windjammer Festival or Jazz in June concerts, blending the comfort of modern amenities with the charm of antique furnishings. Alternatively, visitors can opt for a more intimate and culturally immersive experience at the Blue Harbor House Bed and Breakfast Inn, established in 1870. This delightful accommodation is an ideal starting point for an early morning hike up Mt. Battie or a sunset sail from the local marina, ensuring a memorable and picturesque getaway in the heart of Camden.
Woodstock, Vermont
Chartered in 1761, the town has an array of buildings listed on the National Register of Historic Places, including the home of former President Calvin Coolidge and the visually stunning Norman Williams Public Library, crafted from pink sandstone. The centerpiece of the town is The Green, a lush central park surrounded by historic architecture and crossed by the scenic Middle Covered Bridge over the Ottauquechee River. This setting not only invites leisurely strolls and photo opportunities but also serves as a gateway to explore the charming downtown area. Here, visitors can browse unique local shops like Yankee Bookshop and Woody’s Mercantile, which offer a taste of local culture and craftsmanship.
The Woodstock Inn and Resort on Main Street provides an upscale lodging option that embodies the elegance of the town. This distinguished hotel offers easy access to both the tranquil beauty of the surrounding landscapes and the vibrant life of the town center. Just outside the village, the Billings Farm & Museum presents a fascinating glimpse into 19th-century farm life, while the Marsh-Billings-Rockefeller National Historical Park offers extensive trails and the chance to discover a historic Queen Anne-style mansion. Alternatively, visitors might choose to stay at the Shire Woodstock, known for its picturesque setting and welcoming atmosphere, providing a perfect base from which to explore the winding trails and architectural delights of Woodstock.
Kennebunkport, Maine
Kennebunkport, located just a 90-minute drive north of Boston, is a perfect coastal weekend escape. The town’s heart is Dock Square, where visitors are greeted with a vibrant scene of old commercial buildings that have been transformed into boutique shops, art galleries, and renowned seafood restaurants serving up local specialties. This bustling center provides not only a taste of Kennebunkport’s rich maritime heritage but also convenient amenities like ample parking and restrooms, making it an excellent starting point for any visitor. The area’s architectural charm is complemented by several old inns and B&Bs that offer warm hospitality and a quaint setting for relaxation, including the Kennebunkport Inn and the charming Old Parsonage Guest House, both perfect for soaking in the local culture and comfort after a day of exploration.
For those interested in history, the Seashore Trolley Museum, the world's oldest and largest electric railway museum, provides an engaging look at the region's transportation past with the chance to ride on vintage trolleys. Nature lovers will find plenty to admire at scenic beaches like Goose Rocks Beach and Colony Beach, ideal for leisurely days spent by the sea. Additionally, the Rachel Carson National Wildlife Refuge offers serene trails and excellent birdwatching opportunities, appealing to those who appreciate the outdoors.
Mystic, Connecticut
Mystic’s history is intricately linked to the Mystic River, which not only provided a gateway to the Atlantic but also served as a hub for shipbuilding with over 600 ships constructed here across 135 years. Today, visitors can immerse themselves in this rich heritage at the Mystic Seaport Museum, home to the Charles W. Morgan, the last wooden whaleship still afloat in the U.S. This living museum not only offers a peek into the past with its 19th-century artifacts and memorabilia but also allows guests to experience the seafaring life of yore. For those interested in marine biology and conservation, the Mystic Aquarium & Institute for Exploration presents a chance to engage with a variety of marine species and learn about ongoing efforts to protect oceanic wildlife.
The Steamboat Inn, conveniently located in the heart of the lively downtown area, offers eleven beautifully appointed rooms, each with water views and a cozy gas fireplace, making it an ideal choice for those seeking comfort and scenic vistas. Additionally, for those wishing to stay a bit further from the downtown hustle, the Inn at Mystic provides a more secluded setting with equally compelling amenities and access to local attractions. Whether exploring the historic shipyards, challenging oneself at the Tree Trails adventure park, or simply relaxing by the river, Mystic combines the allure of the sea with the charm of a small town.
Stowe, Vermont
Stowe, known as the "Ski Capital of the East," is at the base of Mount Mansfield, Vermont's highest peak. In the winter, the iconic Stowe Mountain Resort becomes a haven for ski enthusiasts, with slopes renowned for their beauty and challenge. When the snow melts, the area transforms into a hiker's paradise, offering rigorous trails up Mount Mansfield that boast some of the most breathtaking views in the state. The nearby Green Mountains offer gentler hikes, such as the path leading to Moss Glen Falls, a picturesque spot perfect for nature lovers and photographers alike.
Downtown Stowe is a delightful exploration ground with its manicured sidewalks leading to quirky shops like the Country Store on Main and rustic cafes such as Café on Main. Autumn in Stowe is especially magical, making it one of the best places in the country to witness the vibrant fall colors. The town hosts various seasonal events that draw visitors from near and far, including the Annual Stowe Foliage Arts and Crafts Festival and the Leaf Blower Fall Classic at Strawberry Hill Farm. For those planning to stay, Stowe Mountain Resort offers not just exceptional skiing but also luxurious accommodations and amenities, ensuring a comfortable and memorable stay.
New England’s diverse towns, with their rich history, scenic beauty, and seasonal activities, provide the perfect backdrop for a picturesque weekend retreat. Whether you're drawn to the cultural vibrancy of Lenox, the coastal charm of Newport, or the outdoor allure of Stowe, each destination promises a unique and unforgettable experience.
