Romantic Retreat: 15 Things to Do in Woodstock VT for Couples

When it comes to picturesque New England charm, few places rival Woodstock, Vermont, especially during fall foliage season. It’s the quintessential New England village, known for its scenic beauty, rich history, and vibrant cultural life. Whether you’re an outdoor adventurer, a history buff, or someone who simply loves to explore, you’ll find a multitude of memorable things to do in Woodstock, VT.

A tidy downtown anchored by the venerable Woodstock Inn (for 150 years!), Woodstock  VT, and the surrounding area are not glutted with kitsch or tourist fare.

Woodstock was initially a release valve for the Victorian wealthy. They’d take the train from NYC or Boston to White River Junction, and then the 14-mile spur into the mountains. Woodstock still feels romantically lost in time.

This is the region where Calvin Coolidge was born and raised. It’s also where the National Park Service chose to impart the history of land conservation in the US. Add to that great hand-crafted cheese, famous artisans, and a historic luxury inn, and you’re golden for a wonderful weekend.

Where Is Woodstock VT?

Woodstock, Vermont, is situated in Windsor County, amid the Green Mountains. The village is approximately 14 miles west of the White River Junction and about 90 miles southeast of Burlington, Vermont’s largest city. Woodstock serves as a gateway to the scenic Ottauquechee River Valley and is easily accessible via U.S. Route 4.

Looking for more weekend getaway ideas? Here’s our roundup of romantic getaways in New England.

Things to Do In Woodstock VT

History of Conservation

TOUR: Billings Farm Museum and Marsh-Billings-Rockefeller National Historic Site

Plan at least half a day (3-4 hours) to explore these two attractions. They used to be one – until Laurance Rockefeller donated his summer home to the National Park Service in 1992. Purchase tickets for both in the Farm Museum Visitor’s Center. (Schedule changes seasonally, check the website to confirm when open to the public.)

A Place in the Land, Woodstock VT

Begin by watching the award-winning 32-minute documentary; “A Place in the Land.” The documentary clearly conveys the reason this place has so many names and the significance of each.

All three men who owned this home, it turns out, were environmentalists way before their time. In fact, the homebuilder, George Marsh, sounded the alarm about climate change over 150 years ago.

George Marsh

Marsh, born in 1801 in Woodstock watched as 60% of the virgin timber was cut down to clear the land for farming. Floods and erosion followed, and fishes disappeared. Marsh became a lawyer, and then a politician, advocating for the reclamation of rivers.

On diplomatic assignment in Turkey and the Ottoman Empire, Marsh studied the history of the arid land through ancient maps that showed lush forests in the areas devastated by desert. He attributed the fall of the Great Empires to overgrazing and deforestation.

“ I fear that man has brought the face of the earth to a desolation almost as complete as that of the moon,” he wrote in his seminal call to action tome, Man and Nature in 1864 (the very book that influenced “The Father of Conservation,” Gifford Pinchot, years later).

View From the Mansion

While Marsh was overseas, his brother sold the home to Vermont-born lawyer/industrialist, Frederick Billings. Billings had made a fortune in land speculation out West during the California Gold Rush, and invested in the Northern Pacific Railroad and other Western state businesses. (Billings, Montana was named for him).

Frederick Billings

But, like Marsh, Billings was concerned about the damage done to the environment through the clear-cutting of the great Redwoods. He felt that replanting trees and restoration of the land was not only possible but an obligation.

Billings had left Woodstock at age 25, and returned in middle age to implement his ideas. Beginning in 1871, he re-propagated the denuded hills, built his farm as a sustainable model, constructed a nice home for farm and business manager, George Aiken, and oversaw what is now open for visitors- the adjacent Billings Farm.

Frederick Billings died in 1890, but he wished for the farm and home to remain in the family. Unusual for the time, the property was handed down through women. It passed from Billings’ wife to their daughters, to their granddaughter, Mary, who married Laurance Rockefeller in 1954.

Laurance Rockerfeller

Out of all the five children of John D. Rockefeller, Laurance had inherited his father’s commitment to conservation. John D. brought Laurence out west and along the Hudson River Valley to soak in the power of natural, untainted landscapes. Laurance became an advocate for Historic Preservation and land conservation.

He persuaded his brother, Nelson, then Governor of NY, to establish the Adirondacks as a protected State Park, and to expand the system of New York State Parks. He and Mary donated their extensive property on Saint John in the Virgin Islands, as well as their home in Woodstock VT, to the National Park Service.

Marsh-Billings-Rockefeller NHP

Marsh Billings Rockefeller Mansion

The Marsh-Billings-Rockefeller National Historical Park is now the first National Site dedicated to understanding the history of conservation in the United States.

Take a one-hour tour of the manor home (up the hill) that Laurance and Mary turned over to the National Park Service in 1992.

It’s full of Thomas Cole and Hudson River School of Art oils. Take an “Art Tour,” as well as other specialty tours of the home and grounds, which includes the Bungalow, The Belvedere (a “rec” house with bowling alley and soda fountain), and hundreds of acres.

The Marsh-Billings-Rockefeller NHP is one of 10 quirky-romantic places to propose in Vermont.

Billings Farm Tour

Billings Farm Museum

You can also spend many hours at the adjacent Billings Farm, still considered one of the finest dairy farms in America and a museum of Vermont’s rural past. Begin in the museum on the second floor of the Visitor’s Center.

The place is massive. It incorporates dioramas of antique farm tools at work, machinery from the 1800s, a complete cross-section of a farm home and a dry-goods store, a one-room schoolhouse, a sugaring exhibit, and gaggles of school kids engaged in activities (like churning butter).

Tom of Tom and Jerry draft horse team

Meet Tom and Jerry – a pair of sturdy draft horses. Or stumble on cows being milked (or right afterward, when they take a siesta), and view babies in the “Calf Room.”

Though the animal barns are a joy to visit, do make it a point to tour the 1890 Farm Manager’s home (tours every hour), built by Frederick Billings for George Aiken and his family.

On Long Island, Aiken was raising a sturdy, adaptable cow that he’d imported from the Isle of Jersey – a breed that came to be known as Jersey Cows.

He understood that farming could be sustainable, rather than the “subsistence farming” of the time. He “got” what Billings was attempting to do with the land, and moved his wife, four daughters, and his cows here.

Touring the Billings Farmhouse

See the premium butter-making operation in the basement. As a railroad magnate, Billings had the ways and means to ship his proprietary butter all over the Northeast.

The home was outfitted with the most modern amenities, including indoor plumbing. Most fascinating are the three faucets at every sink: hot, cold, and a separate spigot for soft rainwater, pumped from a cistern, that was used for cooking and laundry.

For those who love nature, the national park next to Billings Farm offers an array of hiking trails perfect for viewing fall foliage. You can also bring your mountain biking gear or cross country skis to explore the scenic terrain.

Plymouth Notch Post Office

TOUR: Calvin Coolidge Homestead District/President Calvin Coolidge State Historic Site

Our country’s 30th president was born in a modest rural home and grew up tilling the land. As Vice President, he was thrust into the Presidency when Warren G. Harding died suddenly of a heart attack.

Coolidge presided over “Roaring 20’s” America and exited politics right before the Crash of ’29.

Coolidge Center Plymouth Notch VT

About 13 miles west of Woodstock, all 25 structures that make up the small hill town where Coolidge was born and spent much of his time have been meticulously preserved.

Hence, it is not technically a “living history museum.” Residents from the surrounding area still come to the operating US Post Office for their mail.

Start Tour at the Visitors Center

Calvin Coolidge Museum

Begin at the Visitor’s Center, home to an excellent, interactive museum about Coolidge and his fashionista-wife, Grace. Called “Sunshine” by White House staff for her easy, cheerful disposition, Grace was a teacher for the deaf before meeting Calvin.

She became a favorite First Lady while her husband was in office. Grace was also a voice against Nazi Germany while touring Europe with a friend in 1936.

You’ll see the piano that Grace enjoyed playing – the first piano ever to fly in an airplane. Calvin loved to buy her clothing. One of her more memorable dresses was a ten pound gold-beaded number from Sterns in Boston.

Coolidge was fiscally conservative, but a social progressive. He favored shorter workweeks, and voting rights for women. One of the first Acts he signed into law was the Indian Citizenship Act, granting full U.S. citizenship to Native Americans.

The award-winning museum is divided by stages of Coolidge’s life. Slanted walls make it easier to read and watch videos. You can “Ask Coolidge a Question” – (voice recognition technology at work!), and access over 30 newsreels.

Swearing Into Office By Light of a Kerosine Lamp

Coolidge Commemorative plates

The tiny town of Plymouth Notch (pop 29) became a sensation overnight, when John Calvin Coolidge, Sr., a notary public, swore his son into office at 2:47AM on August 3, 1923 by the light of a kerosene lamp in his family homestead. (The home did not have electricity or indoor plumbing).

A “Quaint” Vermont Town

Plymouth Notch was a “quaint” old-fashioned town, even by 1923 standards. The American populace ate it up. Thousands of tourists came to this little place. Gift shops and ice cream stands opened to cater to them. Shaffordshire of England created custom souvenir plates that sold like hotcakes.

Coolidge Birth Bed

Take a guided tour of the town (on the hour) to see the humble wooden home and bed in which Coolidge was born.  The rustic home was attached to the family’s general store.

The Coolidge’s eventually built a larger home across the street. This is where you’ll find the small study dimmed as it was on the night Coolidge took office.

The crude work-frock that he’d don whenever he did field work hangs on a wall hook. What was so important about that simple garment? It seems that the press came to Plymouth Notch and found Coolidge wearing what he always wore to work the land.

Media reported that the new President was attempting to exaggerate his humble beginnings by throwing on a costume for the cameras. From then on, Coolidge farmed and fished in a three-piece suit – a witty response to those snarky reporters.

The Plymouth Cheese Co.

Plymouth Cheese Co

Before leaving the State Historic Site and the little hamlet of Plymouth Notch, stop at the Plymouth Cheese Factory. Calvin Coolidge’s father founded it in 1890 in this very barn. He managed it well into the ‘30s.

In the 1960s Calvin’s son, John, reopened the cheese-making concern, owning it into the 90’s. In 2009, it was opened again, with Plymouth Cheese much in demand by NYC chefs and specialty cheese shops around the country.

Woodstock History Center

VISIT: Woodstock History Center

The home of the Woodstock Historical Society, in the center of town, is often overlooked by tourists. But this 8-room home of Charles and Mary Dana, built in 1807 right on the river, does have its merits.

Stand on original wide-plank floors. Check out fixtures converted from candlelight to oil to electricity. See the authentic 1772 Town Charter with the seal of King George III. And delight in the variety of early 1800s toys in the children’s room upstairs.

View from History Center backyard

Innovative programs – like free antique appraisal days and cemetery tours complete with re-enactors – bring out the locals and visitors looking for something different to do.

But perhaps the #1 reason you should come here is for the backyard on the river. It’s got the best view of the town’s covered bridge.

Paul Revere Bell, Woodstock VT

SEE: Bell cast by Paul Revere & Sons Foundry at the First Congregational Church

There are five Revere bells in Woodstock, VT. This one is not in use. But it is on display on the steps leading up to the church two doors down from the Woodstock History Center.

FH Gillingham Woodstock VT

SHOP: FH Gillingham & Son General Store

This late 1800’s store is still in family hands. You can still pick up almost anything, from prepared gourmet food to fishing tackle to cutting-edge gifts (maple syrup, anyone?,) and so much more.

In a 1994 piece for the Philadelphia Inquirer, Suki Casanave wrote about Gillingham, “Best of all is the smell inside the store – an aroma of fresh-ground coffee beans, spices, cheeses, chocolate, and well-oiled floors. If someone ever wanted to bottle a scent and call it ‘General Store,’ this is where they’d come get it.”

Woodstock Town Crier

SEE: The Town Crier

For over 60 years, this simple blackboard near the Green has been a central clearinghouse for all Woodstock events. Maintained by the Woodstock Historical Society, you’ll find dates and times of ice cream socials, movies, lectures, and just about anything else going on in town.

WALK: Downtown Woodstock Main StreetsVermont Flannel Woodstock VT

Everyone does. And you will not find one “Big Box” store in town. You will, however, stumble on the wonderful indie Yankee Bookshop and Vermont Flannel, where I picked up my new favorite comfy winter nightgown.

SEE: Famous artisans, Miranda Thomas and Charles Shackleton at work.

In Bridgewater – a few miles west, a renovated 1814 mill houses the busy workshops of world-famous potter Miranda Thomas and her husband, Charles Shackelton. Thomas’s bunny, bird, and floral motifs have won over UN dignitaries and heads of state. And they will win you over, too.

“Simon enticed us to move here,” said Thomas, referring to down-the-street neighbor, glassmaker Simon Pierce whose own workshop is 10 miles away in Quechee.

SHOP/TRY: Farmhouse Pottery

Want to take a turn at the wheel? Learn how to craft pottery at the same place you can shop for high-quality, locally-made pottery.

Vermont Spirits Distillery, Quechee VT

SEE/TASTE: Simon Pierce, Cabot Cheese, Vermont Distillery, Quechee

Stop in to see glassmaker, Simon Pierce, then to the Cabot Cheese annex (lots of samples) before settling in for a few sample sips at Vermont Spirits. I’m a straight-up Vodka gal. But VS’s bestselling No 14 Bourbon won me over to the Bourbon side with a smooth, warming maple finish. You’ll also find Crimson Apple Vodka, Black Snake Whiskey, and Vermont White Vodka distilled from whey.

GO: Quechee Gorge

Just 15 minutes away, Quechee Gorge offers stunning views and the perfect opportunity for outdoor photography. Walk the Quechee Covered Bridge for a panoramic perspective of Vermont’s deepest gorge.

SEE: Middle Covered Bridge & Taftsville Covered Bridge

These picturesque covered bridges are perfect for photo ops and romantic walks. Located in and around Woodstock, they add to the town’s old-world ambiance.

Woodstock VT Restaurants

Worthy Kitchen, Woodstock VT

EAT: Worthy Kitchen

Just a quick drive out of town, in a multi-shop building on a hill, Worthy Kitchen serves up “Craft Beer Farm Diners.” Find Vermont Raised Burgers, Portobello Mushroom Burger on Worthy Bun, specialty burritos and wings (Rootbeer-Sriracha-BBQ!), and 18 craft beers on draft.

The space is fun and funky. Poured concrete communal tables invite convivial conversation. Huge blackboards advertise the beer and food specials of the day. And you order at the counter. Get a buzzer, and wait to pick up your food. Easy. Good. Fun.

EAT: Mon Vert Cafe

Downtown Woodstock is home to Mon Vert Cafe, an award-winning café known for its gourmet coffees and freshly baked pastries. It’s the ideal place for breakfast or lunch.

Long Tail Brewery VT

DRINK/BREWERY: Long Trail Brewery

Stop in to this popular brewery for samples and a quick meal. A bit out of town, it’s a hit with locals and a hoot to tour. Go upstairs to the observation deck to see one of the fastest bottling facilities known to beer. It’s frantic and mesmerizing.

Best Places to Stay in Woodstock VT

STAY: Woodstock Inn

First opened in 1892 on the site of the Eagle Inn, The Woodstock Inn has reason to be proud. Service is exemplary, food is wonderful and aesthetics way over par. Though most amenities – fitness center, golf course, ski resort – are off-site, they are easy to get to.

And if it is just your desire to hang out, get a massage, watch snow fall outside while you sweat in a Dry Sauna (yes, there’s a window!), or catch up with friends and family in the stately “Library,” you can do that onsite as well.

First Impressions of the Woodstock Inn and Resort

Woodstock Inn

I arrived in the heat of summer, but I’d imagine a blazing fire in the huge fireplace would warm that room right up. Service is hop-to-it friendly, from valet to check in. And the Inn’s central location is fantastic.

Guestrooms At the Woodstock Inn

Room at Woodstock Inn

Rooms have been redone with high thread count bedding on billowing cloudlike mattress. Bathrooms gleam with subway-tile walls, white marble floors and vanity tables.

Dining at Woodstock Inn

Richardsons Tavern at Woodstock Inn

Both Richardson’s Tavern and The Red Rooster are well-regarded restaurants in town. The dimly lit, more casual Tavern is a favorite with families. And the bright modern Red Rooster offers more upscale, inventive fare.

If you don’t want a full meal, or just want to spread out, you can order snacks and beverages in the Game Room, at the Pool or in the sunlit Conservatory.

Woodstock Inn Spa

Woodstock Inn Hot Tub and Dry Sauna

This eye-catching 10,000 sq ft. spa was opened in 2010 in a LEED Designed extension of the Inn. Sporting local Bluestone and sustainably harvested Oak, the “Waiting room” faces towards an outdoor saltwater pool. The stand-alone dry sauna building features a window.

It’s the height of warm luxury while snow falls outside. You don’t have to be booked for a treatment to enjoy the dry sauna, or the Eucalyptus-infused steam shower, cucumber water, cold washcloths, mosaic showers, or pool.

Amenities at Woodstock Inn

Woodstock Inn Saltwater Pool

Guests receive free passes to the Billings Farm and Museum, and have access to the Racquet & Fitness Club in town (for tennis, racquetball, and fitness classes).

Woodstock Inn Grounds

The Inn manages its own 18-hole Robert Trent Jones, Sr. golf course in summer and the Suicide Six Ski Resort in winter. The Game Room downstairs is every kid’s dream. Even kids at heart love the arcade games, billiards, checkers, and plenty more. With food and beverage service.

Woodstock Inn Game Room

An additional resort fee offers guests Billings Farm Admission, morning coffee and tea, afternoon tea and cookies, unlimited bottled water, admission to Racket & Fitness Club, Group Fitness Classes, Resort Shuttle, Parking, Wi-Fi, use of bikes, and complimentary day passes to Suicide Six midweek, non-holiday only.

STAY: Farmhouse Inn at Robinson Farm

It will forever be known as “Robinson’s Place.” But owners, Tory and Barry Milstone opened this old farmhouse as a B&B in January 2008 and have since turned it into a worthy destination.

Five guestrooms dressed in lots of quilts, rag rugs, pen and ink drawings, Turkish towels, and luxurious bedding are eclectically tasteful.

Farmhouse Inn at Robinson Farm

A rinse beneath the rain showerhead in the dark slate-tile shower in Stan’s Room transports you to a hidden waterfall. Behind the house, the elaborate four-story 1915 red barn is purported to be the tallest barn in Vermont.

Formerly housing cows and lots of hay, it now accommodates free-range chickens -“the girls.” You can see them muttering and laying on a personal tour of the property.

Farmhouse Inn at Robinsons Farm Property Woodstock VT

I’d venture to say that this is the only B&B in the world with an antique carousel horse in the dining room. Here, partake of a sumptuous breakfast, including backyard ingredients such as syrup tapped from property trees, produce from the kitchen garden, eggs from happy hens, and an occasional trout from the river across the street.


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine,, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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3 thoughts on “Romantic Retreat: 15 Things to Do in Woodstock VT for Couples”

  1. Bently’s, gahhh not that good and way over priced. Lived in Woodstock for 24 years and never once was it good.

    It could however, be considered woodstock only dive bar. Haha

  2. Thanks for catching that. I changed it to “Downtown Main Streets” as per your comment. Thanks for reading.

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