7 Best Vermont Towns For A Weekend Trip
Vermont is a state known for its stunning beauty throughout the year, with vibrant fall foliage, serene summers, and scenic winters perfect for skiing and snowshoeing! With the majestic Green Mountains, the calm waters of Lake Champlain, and top-notch skiing destinations, it’s one of the most beautiful states in the country. Peppered throughout Vermont’s natural landmarks are quaint little towns with friendly locals and so many seasonal attractions! No matter what time of year you find yourself in these cozy hamlets, you are sure to have a lovely time. So, clear some camera space on your phone and get ready to explore these charming Vermont towns.
Grafton
Travel back in time to the days of the early settlers in the historic village of Grafton. Many of the colonial-era buildings in Grafton aren’t recreations, but rather lovingly restored structures that reflect the early days of the area (without losing the amenities of home!). One of its most notable restored structures is The Grafton Inn, which first opened its doors in 1801! With inviting rooms, and a rustic restaurant, staying at the Grafton Inn is a must when visiting the area.
While walking the streets of downtown is a visual treat, there are so many unique stores to discover, like the Grafton Village Cheese Company and The Nature Museum at Grafton. But if it’s real Vermont maple syrup you’re after, Plummer’s Sugar House is the spot to take home real maple syrup! If you love getting out and exploring nature, the Grafton Trails and Outdoor Center offers 2,000 acres dedicated to hiking, biking, swimming, snowshoeing, and sleigh rides through the Green Mountains. As one of Vermont’s most beautiful towns, it’s a great place to relax over a long weekend.
Woodstock
From farmer’s markets to delightful local events in the historic downtown district, Woodstock takes its relaxation very seriously! Situated in the Green Mountains on the shores of the Ottauquechee River at the Crossroads of the Vermont Scenic Byway, it offers some of the most breathtaking views of New England. You can spend the day walking the manicured sidewalks and pop in shops like Clover Gift Shop or Echo Market.
In the heart of Woodstock is the Woodstock B&B, a delightful bed and breakfast that will make you feel right at home in no time. Stay the night (or two) in a modern farmhouse-style inn with made-to-order breakfast every morning in their cheery and bright dining room. After a filling breakfast, you can take a tour of the Billings Farm and Museum and then stop at the Vermont Farmstead Cheese Company for treats to bring back home. From exciting local attractions to comfortable accommodations, Woodstock is sure to transport you back to a time when life is a little easier.
Brattleboro
No matter what time of year you find yourself in Brattleboro, you’re bound to have a wonderful time! From fall foliage tours to sledding and skiing, Brattleboro is like a slice of the good life tucked away in the Southern Green Mountains. It’s not your average New England town it strays from the classic colonial and boasts more modern, artsy vibes. There’s no better example of this than The Latchis, an art-deco hotel built in the 1930s with so much character. It’s a must-see for visitors new to the area, and its amenities and unique style won’t disappoint.
When you’re ready to explore the countryside of Brattleboro, you don’t have to travel far outside the downtown area. Retreat Farm is the go-to spot when you want to bring home authentic Vermont maple syrup. Not only does it sell artisanal goods like syrup and cheese, but this lovely farm also hosts seasonal farmer’s markets, wine tastings, and the Harris Hill Ski Jump Event held every February. Just past the beautiful Creamery Covered Bridge is Living Memorial Park, Brattleboro's beloved green space with hiking trails, swimming pools, ice skating rinks, and playgrounds. It’s hard to enjoy everything Brattleboro has to offer in a single weekend!
Stowe
While much of New England comes alive in the summer and fall, the small city of Stowe lives for the winter. Situated in the shadows of Mount Mansfield (Vermont's highest mountain), Stowe is the premier spot to hit the slopes! While the picturesque village of Stowe has plenty of bed and breakfasts to choose from, the Green Mountain Inn is one of the best! This stately brick manor looks like something out of a Christmas card, and the insides are just as homey as you imagine. It’s the ideal spot to warm up by the fire before venturing out into the cold to ski at the Stowe Mountain Resort.
While Stowe is famous for its winter sports, it transforms into an idyllic nature retreat in the warmer months. The Gondola SkyRide takes you to the tippy top of Vermont atop Mount Mansfield, but it’s not just gorgeous views at the top. From there, you can grab a meal at the Cliff House or a hot Belgian waffle at The Waffle! In the warmer months, the Stowe Mountain resort provides miles of easy-to-challenging hiking trails via the Spruce Peak Community Pathways. Stowe is a place that you’ll want to experience every season of the year!
Waitsfield
Far removed from the noise of the big cities of Vermont in the heart of the Mad River Valley is the small, unassuming village of Waitsfield. Waitsfield may be famous for its ski resorts like the Sugarbush Resort and Mad River Glen, but there’s so much more to see and do than just ski! It’s home to heartwarming bed and breakfasts, like The Inn at the Round Barn Farm, that offer a lovely respite when you need to warm your bones after a long day of skiing or exploring. Built in 1910 and situated on 45 acres of manicured grounds, it’s a delightful stay that's worth the drive.
Waitsfield is also home to charming and unusual attractions, like the Great Eddy Covered Bridge. After a chilly day exploring, it’s a wonderful spot to catch a meal and a show (and maybe one or two of their famous maple donuts!). The Mad River Glass Gallery is a fun and funky studio where you can admire amazing artwork and maybe pick up a piece to take back home to remember your trip! Whether you are in town to watch the leaves change, hike up a mountain, or hit the ski slopes, Waitsfield proves one of Vermont's best-kept secrets for a weekend retreat.
Manchester
It’ll be difficult to experience everything Manchester has to offer in a single weekend, but there’s no harm in trying! With an intriguing downtown district, the natural beauty of the Green Mountains, and excellent shopping, it is a slow-paced town with a little of everything. When shopping in the historic downtown district, make sure to pop in the Northshire Bookstore! Many feel that this rustic bookstore is one of the best independent bookstores in the state. If you’re more serious about shopping, the Manchester Designer Outlets provides a wide variety of shops with excellent prices.
If you’re in Manchester for winter skiing, one of the best places to stay is the Stratton Mountain Resort. You can get a discounted bundle that includes accommodations with lift tickets included. If slow-paced, rustic vibes are what you’re after, there’s no better place than The Inn at Manchester, with its bright, airy rooms and wooded views right out of a postcard. If you love amazing estates, you have to check out Hildene, The Lincoln Family Home, while you are in town. The former Lincoln family home offers guided tours year-round but really comes alive in the winter during the annual Christmas at Hildene. If you can’t fit in every attraction over a long weekend, it just means you will have to come back again!
Shelburne
In Shelburne, you’ll come for the gorgeous scenery and stay for the fun and exciting attractions! Aside from the picturesque landscapes of Lake Champlain and the Green Mountains in the distance, there’s tons to do in this sleepy waterside town. The Shelburne Farms Inn is one of the premier places visitors to the area can stay. Situated along the banks of Lake Champlain, this sprawling inn was built in 1899, and the surrounding grounds cover almost 1,400 untouched acres along Lake Champlain. You could seriously just spend the entire weekend relaxing at the inn and taking in the views of the estate.
While you could technically stay all weekend at the inn, there is too much to see in the area! The nearby Shelburne Museum boasts 25 historical buildings, including an old jail built in the 1830s, as well as a covered bridge and its iconic Round Barn. Or, check out Shelburne Farms, where you can hike the nearby trails or take a tour of the amazing Shelburne house. Don’t forget to stop by the gift shop for real Vermont maple syrup and artisan cheeses! These attractions are also home to seasonal events that often draw crowds from the area. If you need a relaxing weekend that’s peaceful but never boring, add Shelburne to your Vermont bucket list!
Plan your next Vermont getaway
The amazing landscapes of Vermont are perfect for fall foliage viewing, but there’s so much more to the Green Mountain State outside that tiny window of peak autumn colors. You can soak up the sun at Lake Champlain in Shelburne in the summer or ski down Vermont’s highest peak on Mount Mansfield in Stowe in the winter. With scenic landscapes, vibrant towns, and year-round activities, Vermont promises an unforgettable escape for every traveler, no matter the time of year. Just make sure you stop off and pick up some maple candies for the drive home!
