The Dover Oak: 300 years strong

The 300 year-old Dover Oak in Pawling, Eastern Dutchess County, New York is 22 feet in circumference and 114 feet tall.
Jennifer Almquist
The 300 year-old Dover Oak in Pawling, Eastern Dutchess County, New York is 22 feet in circumference and 114 feet tall.
Twelve stalwart middle schoolers, and their intrepid teachers hike annually through a four-mile section of the Appalachian Trail (AT) in Eastern Dutchess County, NY. As they wind their way down the path from a sunny apple-tree filled meadow, they come upon the massive 300-year-old Dover Oak. Since the early 1700s, when the Algonquin tribe still walked the land, its life was contained in an acorn. This Eastern White Oak (Quercus alba), the largest on the length of the Appalachian Trail, the 2,180-mile footpath from Georgia to Maine, has been growing strong and steady. A witness to three centuries of its local history, this ancient survivor has withstood the march of time.
It was a sapling in 1778 when General George Washington blockaded Fredericksburgh, New York, with his 13,000 troops (to keep the British in New York City) and established his Headquarters in the house of John Kane in Pawling, a few miles from the Dover Oak. Surely during our Civil War in the 1860s, the now larger oak gave shelter to Union soldiers in NY’s Fifth Regiment. Then in 1916 when W.E.B. Du Bois and other activists met in the historic Amenia Conferences at Troutbeck, whose purpose was to advance the standing of black citizens in America, (culminating in the NAACP), travelers exclaimed at the breadth of the limbs of the Dover Oak. How does a tree survive de-forestation, being chopped up for firewood, disease, air pollution, drought, and now the impact of climate change?
Your journey on the Appalachian Trail begins at the Great Swamp, New York State’s third largest freshwater wetlands. A bridge allows you to cross the Swamp River, and the hardest part of the trek begins as you head up through the woods. Reaching the top of Corbin Hill, your pathway opens onto the sunny farmland following the perimeter of the fields. Carefully walk down the fieldstone steps, then crane your neck to see the massive limbs of a huge, 114-foot tree reaching skywards above you. You have reached the Dover Oak on West Dover Road in Pawling. This magnificent landmark is on the New York State’s Big Tree Registry as the largest Eastern White Oak.
Jennifer Almquist
To stand near it is overwhelming. Embracing the 20-foot circumference is like hugging an elephant. The sunlight filters down endless convolutions of gnarly bark. You might see a gossamer spiderweb undulating in the wind, catching rainbows from the sun. Squirrels and chipmunks gather on its branches. The base of the trunk resembles the foot of a giant elephant. The surrounding soil is tamped down by the feet of many pilgrims who pay homage to this wonder of nature and survival.
Tom Fahsbender, Director of Experiential Education at the Washington (CT) Montessori School and math and science teacher, has been bringing groups of his middle school students on hiking and backpacking trips on various sections of the Appalachian Trail for the past twenty years. “The trail from the AT train stop on Route 22 to Telephone Pioneers shelter is a favorite of my students, mainly because of the Dover Oak. We generally have about 8 to 10 kids, and the hike is rigorous. After we trek up the hill, over the crest and then slog down through some consistently muddy sections, we climb down a few stone steps and suddenly we are confronted by this glorious, monstrous tree. At this point in the hike the kids are pretty tired, but they get so excited being in the presence of this ancient oak. We spend time talking about its age and all the things that it’s seen, we join hands to measure its circumference and pace out the vast reach of its branches, but mostly the students just like being with the tree. They touch its bark and try to find creatures in the crevices or up in the branches. It is, in the truest sense, awesome.”
Tom Fahsbender
While playing outside in the early post-pandemic days, Berkshire Busk! founder Eugene Carr had an epiphany: why not expand the idea of performing on the street (aka busking)into a full-fledged festival in Great Barrington?
As an entrepreneur and cellist, Carr envisioned a well-organized jamboree featuring regional talent, including musicians, acrobats, storytellers, fire-eaters, and more. He formed a team, connected with local businesses and the town of Great Barrington, and launched Berkshire Busk! in 2021. Since then, Berkshire Busk! has grown into a summer staple for Great Barrington.
In the summer of 2024, over 25,000 people experienced Berkshire Busk!. The festival is free to the public, provides a big boost to local businesses, and spectators can tip performers.
Busking takes place all over the world, either organized by individual performers or via busking festivals. Artists like The Roots, Tracy Chapman, Phoebe Bridgers, and Old Crow Medicine Show have all cut their teeth performing on the street.
General Manager Carli Scolforo is a Berkshire native with a love of music and writing. She can often be seen roaming the streets of Great Barrington, making sure everything’s in order, and serves as the festival’s face on social media.
“This year is the fifth anniversary of Berkshire Busk!, and it’s been an amazing summer,” said Scolforo. “We were able to welcome back a lot of our favorite performers, and bring in some new experiences as well. After getting rained out last year, we were able to host our first outdoor movie night in partnership with The Triplex Cinema and the Boondocks Film Society.”
Scolforo added, “This summer, we also introduced our first Open Mic Night, hosted by local recording artist and music producer Jackson Whalan. We were really pleased with the turnout of talent. The sheer amount of talent that’s hidden within an hour or so drive of Great Barrington always astounds us.”
Local businesses sponsor various busking spots, like the Berkshire Money Management Stage in the parking lot between the Triplex Cinema and Mama Lo’s BBQ. Typically, buskers bring their own amplification, while there are few spots — such as Berkshire Mountain Distillery in Sheffield — provide power.
Berkshire Busk! will end its season with a fireworks display on its last night on Saturday, Aug. 30.
Berkshire Busk! is endorsed by the Select Board of the Town of Great Barrington and is entirely supported by sponsorship fees from companies and organizations, as well as philanthropic donations from granting organizations, individuals and the Town of Great Barrington.
It operates under a fiscal sponsorship agreement with the Nonprofit Center of the Berkshires and participates in Mass Cultural Council’s Card to Culture program — in collaboration with the Department of Transitional Assistance, the Department of Public Health’s WIC Nutrition Program, the Massachusetts Health Connector, and hundreds of organizations — by making cultural programming accessible to those for whom cost is a participation barrier.
For more information, visit: berkshirebusk.com
What if the dog onstage was played by a person? That’s the delightful twist in A.R. Gurney’s “Sylvia,” opening at the Sharon Playhouse on Aug. 29. In this clever and heartfelt comedy, the title character — a stray pup who disrupts the lives of a married couple — is portrayed not in costume but by an actor who brings insight, charm, and chaos to the role.
Stepping into Sylvia’s paws is Jen Cody, who is returning to the Sharon Playhouse in a starring role for her third year in a row, ready to bring this spirited dog to life. She’s joined by Jonathan Walker as Greg, the middle-aged man smitten with his new four-legged friend, and Jennifer Van Dyck as Kate, his wife, whose patience and identity are tested by Sylvia’s sudden presence in their home.
Directed by Colin Hanlon, this production balances elements of comedy and emotional depth. Gurney’s script may be filled with laughs but at its core, “Sylvia” explores loyalty, companionship, and how love sometimes arrives in unexpected forms. The play premiered Off-Broadway in 1995 and has since become an audience favorite for its wit, warmth, and originality.
Rounding out the cast is Sienna Brann, taking on a trio of roles that highlight the play’s comic versatility. The design team includes Christopher and Justin Swader (scenic), Kathleen DeAngelis (costumes), Bobbie Zlotnik (wigs), Wheeler Moon (lighting), and Graham Stone (sound), ensuring the story is grounded in a fully realized world, albeit one occasionally seen from a dog’s point of view.
Performances run through Sept. 7 at the Sharon Playhouse. For tickets and more information, visit sharonplayhouse.org.
Paul Chaleff’s exhibit at Mad Rose Gallery in Millerton.
The unofficial end of summer is here, and while some of us may mourn the shortening days and cooler nights, the culturally-inclined denizens of the Litchfield Hills, Berkshires and Taconics have plenty to look forward to.
During Labor Day weekend, visit one of the offerings below, and maybe even take home a watercolor, rug, or locally-crafted wooden bowl to ready your home for the indoor season ahead.
Kick off the weekend with libations and bites from legendary New York City importer Rosenthal Wine Merchant at Mad Rose Gallery (5916 North Elm Ave., Millerton). The evening will mark the end of Paul Chaleff’s ceramics exhibition, which closes at the end of the weekend. Ashley Gilbertson and Franco Pagetti’s photography exhibition “Fragments in Time,” which has been extended through Sept. 21, will also be on display.RSVP by emailing info@madrosegallery.com.
Head to the Cornwall Library (30 Pine St., Cornwall) for its seventh annual weekend-long Art Sale, and peruse an endless supply of prints, posters, watercolors, photos, paintings and more, with price tags ranging from a very reasonable $20 to much greater sums.
The Library has announced that this year’s selection will “run the gamut from the antique to the contemporary, from the jazzy and colorful to the classic black and white, from realistic to abstract.” Thanks to generous donors, the sale will feature works from notable artists such as Amedeo Modigliani, Enrique Chagoya, Marc Simont, Leonard Baskin, Ruth Gannett, Robert Andrew Parker, Nicole Eisenman, R. H. Quaytman, and others, as well as a special exhibition of vintage photos, paintings and posters from late artist Duncan Hannah.
For more information and hours, visit cornwalllibrary.org/labor-day-art-sale/.
Visit the Barn at the Pine Plains location of beloved antiques and décor purveyor Hammertown (3201 NY-199, Pine Plains) and find the coffee table of your vintage dreams this weekend. Up to 75% off home goods and furniture of all kinds will be available.
This year’s iteration of the biannual tent sale features a “Makers Market” with local artisans, craftspeople and food vendors.
Visit https://shop.hammertown.com/blogs/journal/hammertown-labor-day-tent-sale for additional details and hours.
The Berkshire Woodworkers Guild, a coalition of local woodworkers that supports the local industry and its craftspeople, is hosting its 25th Fine Woodwork Show at the Berkshire Botanical Garden (5 West Stockbridge Rd., Stockbridge) this weekend. Attendees will have the chance to watch 32 masters from around the Tri-Corner region demonstrate their trades, from woodturning and Chinese joinery to boat building and French polishing.
The event will also announce the allocation of $32,000 from its scholarship fund to support 9 aspiring woodworkers, and host a silent auction of guild member-crafted pieces to support next year’s fund. Works from the artisans will also be available for viewing and sale.
Pittsfield, Massachusetts’ Hot Plate Brewing will provide frothy, local ales for swilling, while SoCo Creamery of Great Barrington will be pedaling its handcrafted ice cream for sweeter options for the whole family. Great Cape Baking Co., from Dover Plains will offer a full breakfast and lunch menu, including donuts, while Pleasant & Main from Housatonic will be providing the caffeine and crepes.Further details can be found at berkshirewoodworkers.org.
Artists across Cornwall will fling open their studio and gallery doors to welcome Labor Day culture ramblers on Saturday afternoon. An eclectic lineup of ten participating artists will show their work, ranging from pottery to sculpture paths, allowing participants a chance to enjoy the fresh late-summer weather as they meander through Cornwall’s green valleys from studio to studio.For a list of the artists, a map, and directions to each studio, visit ornwallct.org/event/cornwall-open-studio-2025/.