A weekend in Vermont (especially in Fall) is as perfect as you’d imagine. Cute covered bridges, delicious artisanal stores, restaurants overlooking waterfalls, and scenic drives wait for you. Based around the gorgeous Arlington Inn and Spa, this itinerary has suggestions for the best places to eat out, hikes, and where to get the best views. Enjoy maple, mountains and monuments on this fantastic weekend road trip in the state of “Freedom and Unity”.
Where to stay on your weekend in Vermont
Arlington Inn
The Arlington Inn & Spa makes a wonderful base for a Vermont weekend, because it blends historic charm with modern comfort. Set in the heart of Southern Vermont, it is a perfect stop on your New England road trip, or just for a weekend away.
Within easy reach of Manchester’s shops and dining, the Green Mountains’ hiking trails, and Bennington’s history and culture, it offers a quiet retreat to return to each evening. With beautifully restored rooms, a delicious breakfast included each morning, and an on-site spa for extra relaxation, it’s the kind of place where you can slow down and savor the experience.
During our visit we stayed in the old parsonage adjacent to the main building. Originally built in 1830, it was like stepping back in time and reminded me so much of my great-grandmothers home. Much of the home, especially the outside, is original. However, the amenities (such as the bathroom and shower) are updated and modern. We enjoyed having a kitchen with a refrigerator and coffee pot for those early mornings. The patio out back was perfect for an evening with wine or early morning with coffee.
Disclaimer: We were guests of the Arlington Inn & Spa, however, as always, all opinions are our own.
Where to visit on a weekend in Vermont
Vermont has lots of fantastic places to visit for a weekend. But if you are coming from Boston, we recommend an easy loop of southern and eastern Vermont, between Hanover and Bennington. This area has the Green Mountains, great leaf-peeping opportunities, and lots of covered bridges and cute towns.
Quechee
Quechee is an adorable small town in Vermont located very close to Hanover, New Hampshire. The town itself is so inviting and friendly.
A visit to Simon Pearce is an absolute must. Simon Pearce is a glass blowing manufacturer. Here, you can watch the art being made up close and browse the showroom full of unique pieces.
There is also a restaurant on site offering the most delectable dishes and amazing views of the waterfall just outside. If you have an option, choose the screened in dining area with direct views of the covered bridge. Upstairs you will find a Whistle Pig tasting room too.
Other places to visit in Quechee are the Quechee Gorge and the Quechee Bridge. The 165-foot gorge is known as the state’s “Grand Canyon” and the crown jewel of the state park. The bridge is located inside the state park in conjunction with the gorge. This area is located less than 2 miles from Simon Pearce.
My only regret is that we didn’t have more time to explore this area – definitely add in an overnight in Quechee if you can.
Arlington & Chiselville
Arlington is another small town of Vermont with so much to offer. As soon as we checked in to the Arlington Inn and Spa we were off exploring.
Within a 5 minute drive of the Inn we discovered the Chocolatorium – with “Cocoa”, its 5′ 8″ tall chocolate teddy bear. This place is every chocolate lovers dream. Payton and John had trouble deciding how much to take home.
Not far from here is Chiselville (yes, a town known for the manufacturing of high quality chisels), and it’s gorgeous red covered bridge.
Equinox Skyline Drive
Arlington is the perfect base location for exploring Mount Equinox Skyline Drive, the highest peak in the Taconic Range. The drive is breathtaking with many pull off spots to stop and take in the views.
At the summit, 3,848 feet high, you will find 360 degree views and a visitors center packed full of information. There are multiple viewing points located here as well as the start of the 1 mile hike. From here, on a clear day, you can see Vermont, New York, New Hampshire and Massachusetts.
Restrooms are located here and snacks are available for purchase. You need to allow yourself one hour minimum to explore from beginning to end.
TO NOTE: We arrived at 4:15 only to be told that the last car up was at 4pm. We had to push back our drive until the following morning, which delayed our onward journey a little. Entrance hours vary by season so be sure to check the current times prior to your visit!
Hildene
Also located on the historic route 7A near Arlington is Hildene, the Lincoln family home. This property includes 412 acres, 12 miles of trails, a 600 ft floating boardwalk, a working farm, the 1905 summer home of Robert and Mary Lincoln and a 1903 restored Pullman Palace railcar.
Hildene is a nonprofit organization dedicated to carrying out the values of Abraham Lincoln to future generations.
Covered Bridges
Vermont is home to more than 100 authentic covered bridges. That is more than any other location in the world. We stopped at every one we passed to take photos and to read more about the history of the bridge – it was fascinating.
There are some that you are still able to drive through. Others are pedestrian only. Pay attention to traffic while touring the bridges – and follow the rules for usage. Locals still use them for everyday commuting!
Bennington
Bennington is located just 20 minutes from Arlington and is home to a museum dedicated to covered bridges, as well as the Bennington Monument and Museum.
As a homeschool / history-loving family, this place was a jackpot. Here we learned more about Brigadier General John Stark, Colonel Seth Warner, the Green Mountain Boys, and the battles in and around Bennington.
The Bennington Monument was built completed in 1891 and stands 306 feet tall, resembling the Washington Monument. It is located at the head of Monument Avenue in Monument Circle.
Inside the monument you will find a diorama full of artifacts and information. There is an elevator to access the observation deck where you can see the valleys and hills of Vermont, New York and Massachusetts.
Next to the monument you will find a gift shop on the very site where the continental storehouse once stood. Monument Avenue contains 27 historic sites that you can walk or drive through.
Where to eat on your weekend in Vermont
- Simon Pearce – restaurant located within the glass blowing facility offering amazing dishes and unforgettable views. Make sure to enjoy the cheese plate with multiple cheeses from Vermont and the Vermont cheddar soup.
- BRONWYN on Battenkill – located between the Green and Taconic Mountains on the banks of the Battenkill River, BRONWYN offers authentic German dishes. My best advice is: order to share – the portions are massive and the food is incredible. We enjoyed the warm pretzel, the Spätzle, the Schnitzel, and the Sauerbraten along with duck knödel.
- The Silver Fork – An intimate, upscale spot set in a charming old library in Manchester VT. The Silver Fork blends global flavors with Vermont’s finest local ingredients – reservations recommended!
- SoLo Farm & Table – A true farm-to-table gem where nearly everything on the menu is sourced from nearby farms around South Londonderry. Expect a warm, rustic setting and a menu that changes with the seasons.
- The Dorset Inn – Vermont’s oldest continually operating inn, known for its cozy tavern and elegant dining room. Classic New England comfort food meets fine dining – from maple-glazed duck to house-made soups and desserts.
Vermont Maple Syrup
Vermont maple syrup is one of the state’s most iconic products, prized for its rich flavor and made from sap harvested each spring from the region’s sugar maples. Driving between Quechee and Bennington, you’ll pass through prime “maple country,” where roadside stands, country stores, and family-owned sugarhouses sell syrup directly to visitors.
A standout stop is the Sugar Shack in Arlington, located right along Route 7A. Not only can you sample and buy pure Vermont maple syrup here, but the shop also offers maple candies, pancake mixes, and other local specialties, making it an ideal place to stock up on authentic Vermont flavors during your drive.
A Perfect Weekend in Vermont
Vermont is one of those places that surprised us – it was beyond our expectations by far. Our only regret is not having more time to explore – but this was very much a taster trip, and we know we’ll go back again soon. The small towns, the history, the food, the sights and the covered bridges – it is the perfect place to unwind, reconnect and to get out and explore.
Personally fall is the best time to visit as the weather was absolutely perfect. For skiers, there are so many ski resorts available in winter. When we return it will be for much longer than a weekend.
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