Best Small Vermont Towns for a Weekend Getaway

I love nothing more than small towns… The type of place where you can explore the whole town without getting in your car. Where locals look you in the eye and engage you in conversation about more than just the weather. Where you can visit for a weekend and get a true sense for what the community is really all about. With 251 towns comprising the Green Mountain State, Vermont has endless small town destinations that make for relaxing weekend getaways. Whether you’re visiting Vermont from the Big Apple or Beantown, or simply want to explore another part of your home state, here are the best small Vermont towns for a weekend getaway. Each small Vermont town will make you feel welcome, help you unwind and re-engage with what really matters most in your life. What, in your opinion, are the best small Vermont towns for a weekend getaway? Share in the comments below.

Best Small Vermont Towns for a Weekend Getaway

Warren, Vermont
Whenever someone asks me where they should head for a long weekend in Vermont, the Mad River Valley always tops my list. I love everything about the Valley: the restaurants, the ample hiking-biking-skiing, the mountain vistas, the ready access to Vermont’s best craft beers, and most of all, the happy people who make it their home. Warren, located off of Route 100 with a population of roughly 1,700, is a local’s town. Set on the Mad River, the town consists of the “Almost World Famous” Warren Store and The Pitcher Inn, along with an art gallery, a real estate company, a chocolate-maker and a post office. Every chance I get, I hop over the Appalachian Gap (or this time of the year when the ice has finally melted, the Lincoln Gap) to pay Warren a visit. There’s just something utterly comforting about the quaint town that takes me back to simpler times.

It’s no secret that I have a love affair with The Pitcher Inn and it’s two restaurants, 275 Main and Tracks. The hospitality, the food and the calm the place creates within me is largely unmatched in Vermont. The Relais & Chateaux property, one of two in Vermont, really is a sanctuary. I could spend all day writing, thinking, conversing in any of the uniquely decorated rooms. It’s the ultimate romantic weekend getaway. It is pricey but for the respite from the real-world it offers, it’s worth the investment. (Pro tip: Visit in the off-season—mud season, stick season, bud season—to save enough on a room to pay for dinner on site…)

Have a leisurely breakfast at The Pitcher, even if you’re still thoroughly satisfied from dinner the night before. Read the paper. Converse with your partner. Ask Ari, The Pitcher Inn’s General, how to get to the waterfall hike within walking distance of the inn (his dog-walking hike). Take photos on the cover bridge. Wade in the Mad River. Return and have a snack at the Warren Store, but only after perusing the top floor with its many unique Vermont-made gifts and the Parade Gallery next door to take some Vermont artwork home. Play pool or shuffleboard in Tracks lounge. Enjoy afternoon tea, perfect tea cakes, cookies and finger sandwiches, and try to crack a Stave puzzle in the library. You’ll want to spend ample time in your room too. Between the luxury linens, steam showers and comfy sitting areas in many rooms, you will never want your weekend getaway to come to an end… And when it does, you’ll be planning your next escape back for more. Trust me.

Douglas Orchards, Shoreham, Vermont
Shoreham, Vermont, literally located on the shore of Lake Champlain in Addison County at the intersection of Route 74 and Route 22A, is home to 1,200 residents. It’s the perfect small town for a weekend getaway in Vermont if you’re looking to explore apple orchards, green space and the lake without a set list of activities. It’s even better if you visit in the warm months and bring along your bicycles to explore on two wheels.

The Shoreham Inn, which was built in 1790, is the only game in town when it comes to lodging and dining. It just so happens that it’s superb! Molly and Dominic, owners, innkeepers and wonderful people all around, dish up English-inspired pub fare with a menu that changes daily. The rotating flatbread or caprese salad are my go-to appetizers. The oversized burger, which is more like meatloaf in its flavor composition, is a steal at $11, paired with herby chipped spuds. The mashed are so good you might just end up getting a bowl for $4 for dessert (I’ve seen this happen…). To complete you meal, you must try Banioffi Pie; it’s my favorite, comfort-food dessert in all of Vermont. Switchback and Guinness are the only two draft beers on tap, so I always opt for a black and tan, which complements the pub menu. The inn itself has seven rooms and a recently renovated sheep barn with three two-story loft suites that are more modernly decorated and private than rooms in the main inn.

Depending on the season, be sure to visit Douglas Orchards while in Shoreham for amazing pick-your-own raspberries, blueberries and apples. Champlain Orchards, which is making some of the best hard cider in Vermont, is also in town. Love the water? Hop on the 60-foot Carillon Cruise boat to explore Lake Champlain or take the Fort-Ti Ferry over to Ticonderoga for a historical visit to the 18th century star fort in the narrows of the lake. To round out your visit, head to Norton’s Gallery of Wood Carvings to browse impressive carvings ranging from two-inch birds to five-feet tall dog carvings! (Fair warning: You just might take one home… They’re like puppies like that.)

Pittsfield, Vermont
Tiny Pittsfield, Vermont, has a population hovering around 400. Located on Route 100 between Stockbridge and Killington, Pittsfield is one of Vermont’s most charming towns. The small town made national news in 2011 when Hurricane Irene left residents stranded without any way out due to roads being washed away from flooding. Pittsfield truly epitomizes the essence of community, as neighbors banded together to ensure everyone’s safety during the natural disaster. Now, the up-and-coming visitor destination is gaining popularity for weekend getaways and weddings in Vermont, as well as outdoor adventures, including the Peak / Spartan Death Race.

Amee Farm Lodge is one of my favorite inns in Vermont and is Pittsfield’s best lodging option. The restored inn’s exterior is gorgeous with the perfect balance of local slate and rich woods, as well as an oversized porch to take in expansive views to the east. Inside, the post-and-beam inn is rustically charming. Yes, the hardwood floors squeak. The wood railings in the “modern” addition to the inn are artwork in-and-of-themselves. The 40-acre property offers 15 country rooms. Splurge on Goodrich for the privacy its offers, along with vaulted ceilings and a two-person slate shower with five(!) shower heads. A place where doing nothing is everything, take in the views on the porch at Amee Farm and reconnect. Should you feel up for a bit of activity, there’s a ping pong table on the first floor for a bit of friendly competition.

Sweet Georgia P’s farm stand across the road from the Lodge is worth a visit—you might even get to visit with their sweet goats. Stretch your legs on  the Green Mountain Trails, 25 miles of terrain for train running, biking or snowshoeing. Less than a mile down the road is Pittsfield’s Original General Store where you can find old-time penny candy, an underground wine cellar and tons of Vermont products. Out back of the General Store is The Backroom, a communal dining experience with superb food that you need to experience. Lastly, don’t miss one of my favorite dive locals’ bars in Vermont: The Clear River Tavern. Affectionately known as “The Clear,” it’s the hotspot for nightlife in Pittsfield. The burgers and pizzas to-go are surprisingly delish, and there’s often live music to complement the pool tables and horseshoe pits.

Barnard, Vermont - Best Small Vermont Towns for a Weekend GetawayBarnard, Vermont
Chartered in 1761, the quaint town of Barnard, which is located on Route 12 between Bethel and Woodstock in Windsor County, is home to roughly 1,000 people. Barnard has become a popular destination for a rural getaway due to Twin Farms, an all-inclusive Relais & Chateaux resort and spa located on 300 secluded acres. With 20 custom-designed accommodations to choose from and the ability to customize everything about your experience, Twin Farms is bucket-list worthy, especially for a romantic weekend getaway. Although spendy, everything is included, from hearty breakfasts and picnic lunches to farm-to-table dinners, fully stocked refrigerators, complimentary Stave puzzles and same-day laundry service. Twin Farms is the type of peaceful, fully relaxing place you don’t leave for a weekend. Explore the property, and enjoy each other’s company as well as the luxurious, yet unpretentious setting. Oh, and leave your suit and tie at home… Twin Farms is still in Vermont, after all; be comfortable in whatever you’d like. Anything goes.

While in Barnard, don’t miss the Barnard General Store, which has a heartwarming 183-year history, as told by The Huffington Post. Spend some time perusing the shop for many Vermont-made treasures. Max’s Tavern located at the Barnard Inn Restaurant is also worth a stop for its extensive Vermont craft beer menu and comforting pub fare.

Dorset, Vermont
Dorset, Vermont, is a historic village on Route 30 with long views of the Taconic Mountains in Southern Vermont. Home to the oldest marble quarry in the United States, Dorset has a population of roughly 2,000 residents and embodies everything I equate with a quintessential Vermont town: a rich history, a family-run general store, stately inns that beckon you to come inside and widespread peace and quiet.

The Dorset Inn and The Barrows House are two of the most prominent inns in Dorset with rich local histories. Both are beautiful architecturally and offer modern accommodations that are fitting for a classic Vermont inn. Both also have on-site eateries as well, which are best dining options in town with a happy and accommodating team. The Barrows House, which was renovated and re-opened in 2013, is located on six acres in town and boasts private cottages and a swimming pool for total relaxation. After all, the whole point of visiting these inns and Dorset is not to rush but rather to sit, enjoy and take in all that Vermont has to offer.

H.N William’s General Store, a family-owned and operated country store since 1840, takes you back in history and has anything you could possibly need on its three floors. The Vermont general store is also home to the Dorset farmers’ markets, which run on Sundays, in season. From June through September, don’t miss the Dorset Theatre Festival, which strives to “create bold, innovative and authentic theatre that engages a diverse, multi-generational community.” If you feel like exploring the outskirts of Dorset, Manchester is only six miles down the road and home to Hildene, the Lincoln family home and the Southern Vermont Arts Center, along with outlet shops and countless other notable activities… (But, really, who comes to Vermont to shop generic outlets?) Explore Vermont and its small towns for near experiences and maybe just a new discovery about yourself as well.

What, in your opinion, are the best small Vermont towns for a weekend getaway?  Share in the comments below.

2 replies »

    • Rochester is a great one! I love, love, love Sandy’s BLT and breakfast sandwiches. Doc’s is such a fun spot too!