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Taking the train for a fun day in Rutland that might leave you saying ‘Whoopie!

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Taking the train for a fun day in Rutland that might leave you saying ‘Whoopie!


RUTLAND ― Vermont certainly has its popular tourist destinations. The lakeside city of Burlington, the state capital of Montpelier and the mountain town of Stowe all rank high on the traveler’s to-do list.

But what about Rutland? It’s a city of 15,000 people that’s known for its marble industry and, well, not much else. It does attract out-of-towners drawn in summer by the Vermont State Fair and in winter by the nearby Killington Ski Resort. Otherwise, Rutland rarely registers for those planning a grand Vermont tour.

Every place has its charms, though, right? And with Amtrak service now connecting communities along Vermont’s western half, why not hop down from the Champlain Valley to the heart of central Vermont? Much as I did in the spring when I took the train from Burlington to spend a delightful day in Middlebury, I thought it’d be fun – yes, I’m using “fun” and “Rutland” in conjunction − to take the train from Vergennes and hang out for a few hours in a city that’s often more maligned than celebrated.

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I mean, they had me on this sweet mid-September day with three words – “Whoopie Pie Festival.”

9:05 a.m., Vergennes Laundry

My wife drives me to this busy little city where even on a Saturday morning it’s hard to find a parking spot. We head to Main Street and Vergennes Laundry, a bakery/café I haven’t been to in a half-dozen years.

We each order coffee and an eggs Benedict dish with miso hollandaise sauce, shiitake mushrooms and fried capers. A jazzy soundtrack colors our meal that’s more demure than the heavier eggs Benedict dishes we’ve had elsewhere. The astonishingly fresh brioche that supports the ingredients floats rather than sinks in the stomach. Vergennes is one of my favorite Vermont food towns, so it’s the perfect start to my day.

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10:05 a.m., Ferrisburgh/Vergennes train station

My wife drops me off at the adorable little train station near the intersection of U.S. 7 and Vermont 22A. As the train arrives I see someone I know and mention that I’m heading to Rutland for the day. He tells me to have a great time. The natural joke I make in response is, “I could be the first.”

I know instantly that I didn’t mean that, that I’m playing lazily into the ironic nickname for Rutland, “RutVegas,” which suggests the city is the exact opposite of glitz and glamor. As an unglitzy, unglamorous person myself, I’ve always enjoyed my time in Rutland, especially at the Paramount Theatre where I’ve seen concerts by Chris Isaak, Lyle Lovett and John Hiatt, a one-man show by William Shatner and a production of “Death of a Salesman” starring Christopher Lloyd.

I’ve always felt like Rutland gets a bum rap. Now is my chance to prove it.

10:24 a.m., leaving Vergennes

The train departs on time with me and a handful of fellow Vergennes passengers joining a smattering who came south from the train’s start in Burlington. The car I’m in is facing backwards as we move; is that another bad Rutland joke, that I’m heading back in time by going there?

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While I ignore Amtrak’s wonky Wi-Fi, I look out the window and refresh my love for trains. I admire the beautiful countryside with its mountains and blue skies and green fields.

I also stare into nothingness. The lulling roll of the train and the knowledge that I have no duties for the next hour-plus other than to literally and figuratively be taken someplace else is supremely freeing.

11:30 a.m., Vermont Farmers Market

We arrive five minutes ahead of schedule and I get off with several other passengers who also apparently think Rutland is a worthy destination. I walk through the train station and see that the Vermont Farmers Market I encountered on a previous Saturday-morning Amtrak layover is in full swing across the parking lot.

The Butterfields, an easygoing folk duo, play as hundreds of people stroll by tents that offer grass-fed beef, baked goods, “authentic” Mexican food, Thai food, sushi, deep-dish pizza, gourmet caramel, homemade dog treats, freeze-dried candy, “authentic” Indian cuisine, fruit and vegetables, honey, all-natural oven-baked empanadas, maple syrup, lamb meat, goat cheese, bison meat, coffee and organic pasture-raised eggs.

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Not hungry? You can buy leather hats and bags, jewelry, carved wooden plaques depicting characters from “Sesame Street,” knitted trivets shaped like koala-bear heads, fragrant candles, greeting cards and a painting of a bald eagle perched on a tree branch in front of an American flag,

I capitulate to the call of rampant commerce and buy six sugar-doughnut balls for $5 from the Stevens Farm Fruits and Market booth. I alight in the midday sunlight on an Adirondack chair behind The Butterfields and nosh on my baked goods as the folk duo wraps up a rendition of “Take Me Home, Country Roads.”

I wander off and discover a mural showing all sorts of fruit and veggies, paying homage to the farmers market I just left. I pass a woman on stilts who says, “Hiya,” or maybe “Higher” given her elevated stature. I assume she’s part of the festivities connected to my next destination ….

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12:15 p.m., Whoopie Pie Festival

Today is the third-annual Whoopie Pie Festival that closes off Center Street and Merchants Row, two of the primary thoroughfares downtown. The chocolate-cake-and-cream concoctions are strongly associated with New England – it’s the official State Treat in Maine – and while I don’t know of a connection Rutland has to whoopie pies, any excuse for a party works for me. Plus, it’s fun to say “whoopie.”

I don’t see any whoopie pies as I enter Merchants Row. I encounter several food trucks and a “Ghostbusters” display with a sound system playing instrumental versions of the film’s theme song interspersed with the “Star Wars” theme. I find the musical juxtaposition jarring until I realize that just past the giant inflatable Stay Puft Marshmallow Man there’s a “Star Wars” set-up featuring a towering Chewbacca, stormtroopers and a grown man in a Jedi robe clutching a lightsaber in one hand and a stuffed Yoda doll in another.

I reach Center Street and immediately stumble upon an ambulatory inflatable shark (the Land Shark of “Saturday Night Live” fame?), a chaotic bouncy house, a barbecue food truck called Hangry Hogg depicting an apparently cannibalistic pig brandishing a grilling fork, and, a few steps later, the stilt woman from earlier. It’s all phantasmagorical, like I woke up in a 3-D David Lynch film.

As I head down the street I again encounter the stilt woman (Jennifer Berry of Burlington, I learn) dancing in front of the Paramount Theatre as the Pan-handlers Steel Drum Band plays “Margaritaville.” I pass a man wearing a hat shaped like a whoopie pie but have yet to see any of the festival’s actual treats.

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A little later I find the whoopie pie zone. It’s a mob scene. People line up to sample whoopie pies with the chance to vote for their favorites. I go to the ticket booth where a woman tells me tickets are $1 for any of the 17 vendors. I buy three and ask what’s the most anyone has purchased. She says five. I worry that three might be pushing it.

I scour the booths to determine which three whoopie pies are least likely to sit in my belly two hours later like a big lump of sugar. Many vendors offer variations with pies including pumpkin and peanut butter flavors. I’m homing in on the classic chocolate-cake exterior with white cream filling.

Two of the samples I eat are wedges cut from larger pies with cream filling that’s too sweet for my taste. My favorite of the three is from a booth called Time Out for Whoopie that I’m drawn to partly because of the risqué name but also because they’ve got mini-whoopie pies, not just bits of larger pies. This seems more, as they say, “authentic,” and yummy, too. Time Out for Whoopie, based in Essex, gets my vote on the paper ballot I return to the ticket booth.

After an hour of whoopie-pie tasting and weary from erratic crowds of sweets-seekers veering off to one booth after another, I’m ready for a break. Clearly, I need more food.

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1:42 p.m., The Rollin’ Rooster

I’m back on Merchants Row at The Rollin’ Rooster food truck. As a fried-chicken aficionado, I’ve been eyeing this Pittsford-based eatery for a while. After ingesting sweets for the past couple of hours I just want something small. The clerk at the truck window suggests the Little Chickee is the right choice. I get those two chicken tenders with waffle fries, a bottle of water and a side of honey-mustard dipping sauce for a reasonable $12.

My one quibble with Rutland is there is almost nowhere to sit and eat outside on this food-filled day. I walk back with my meal to the farmers market, where The Butterfields have moved onto “Can’t Buy Me Love” (love is the one thing I didn’t see for sale at the sprawling farmers market). The Adirondack chairs sit squarely in the hot sun, so I head behind the train station and station myself on the steps in the shade along the tracks.

When it comes to fried chicken I prefer bone-in to chicken sandwiches or tenders. These tenders, though, are everything most chicken tenders are not – plump, moist and fresh, the best ones I’ve ever had. I enjoy them while taking in the wafts of creosote and the inelegant industrial decay beside the tracks.

2:50 p.m., Speak Easy Café

After food and snacks and lots of walking I need a caffeinated pick-me-up. I find the Speak Easy Café on Center Street where the good-looking pastries do not tempt me but a 12-ounce Vermont Coffee Co. coffee does. I sit at a table depicting, for reasons I don’t fully understand, George Orwell, and relax with my coffee and a cup of water.

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With no seating to be had outside, it’s nice to find a chair and a bit of air conditioning inside. I overhear a conversation between two women and a guy in dreadlocks who has a French bulldog named Chico on a leash. They’re discussing, what else, the Whoopie Pie Festival.

“It’s a little bizarre,” the dreadlocked guy says to the women. He adds that the festival is also kind of cool. He’s right on both counts.

4 p.m., Whoopie Pie Festival awards

I decide to sate my moderate emotional investment in the whoopie-pie contest. Staff from the Chamber & Economic Development of the Rutland Region dole out prizes from a stage near the convergence of Merchants Row and Center Street.

Professional judges award prizes for most creative and best overall to Cookie’s Cupcakes from Otis, Massachusetts. The People’s Choice Award – the one where I voted for Time Out for Whoopie – went to Sweet Birch Coffee Roasters and Bakery in Wallingford. I didn’t taste samples from either of those bakers, so I’m mildly disappointed.

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Not as disappointed as the woman from Cookie’s Cupcakes. Soon after she walks off with her glass awards, I hear crash behind me and a gasp from the crowd. One of the prizes fell to the pavement, and she and members of the crowd pick up the literal pieces. The phrase “That’s the way the cookie crumbles” enters my head.

Our moods improve quickly as the weigh-in begins for Rutland’s attempt at the world record for largest whoopie pie. The record, by a bakery in Maine, is 1,067 pounds. Dream Maker Bakers of Killington is vying to smash that record.

A construction vehicle lifts the massive pie and the table it sits on and takes measurements. After subtracting 112 pounds for the table, observers announce the results: The whoopie pie weighs in at 1,187 pounds – a new record. A cheer erupts. Pride at gazing upon the world’s largest whoopie pie as it’s held triumphantly aloft swells through the crowd. The bakery hands out samples of the now-famous pie, but I decline. I’m whoopie-pied out.

As I leave the festivities I stop by the Cookie’s Cupcakes booth. A woman there tells me the chamber has already promised to replace the shattered best-overall prize.

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4:20 p.m., sculpture trail

On a past Amtrak layover in Rutland, I picked up cards promoting sculpture and mural tours downtown. I decide to follow the sculpture trail, starting on West Street with one dedicated to Revolutionary War spies Ann and Solomon Story. Nearby I discover a statue not on the official walking-tour brochure that pays homage to Rutland’s renowned Halloween parade with a Batman-esque caped crusader shaking hands with parade founder Tom Fagan.

Most sculptures are concentrated on Merchants Row and Center Street. One honors Paul Harris, a Rutland County native who founded Rotary International. Another pays tribute to Rudyard Kipling, who lived in Dummerston and wrote his most-famous story, “The Jungle Book,” in Vermont. Others salute the 54th Massachusetts Regiment consisting of African-American Civil War soldiers, some of whom came from Vermont; Olympic gold medal-winning skier and Rutland native Andrea Mead Lawrence; Vermont native and Alcoholics Anonymous co-founder Bill Wilson; and Rutland-born Martin Henry Freeman, who became the first African American president of a U.S. college.

Perhaps the centerpiece of the tour is a statue of a man clutching a chisel. “Stone Legacy” honors immigrants from Ireland and Italy who came to use their skills in the region’s marble quarries. Maybe Rutland is no Las Vegas, but it is rich with history and public art.

“Stone Legacy” stands near a stunning mural titled “We Who Believe in Freedom Cannot Rest Until It Comes.” The large painting depicts an African American girl with a sunflower as petals blow into the wind. The mural is on the building that houses Roots the Restaurant, which has a patio with diners enjoying the sunny mid-September weather along the spacious, park-like lawn that holds the Wilson, Freeman and “Stone Legacy” statues. Rutland, it turns out, can be downright idyllic.

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5:15 p.m., Hop ‘N Moose

I go to Hop ‘N Moose, the house brewpub for one of my favorite Vermont beers, the rich Rutland Red ale. (I’ve never understood the placement of the apostrophe in Hop ‘N Moose, but that’s another story for another day.) I sit at the bar and order that and a plate of eight lemon-pepper chicken wings with carrot and celery sticks.

I dig chicken wings, and the ones that really kicked off my fandom were lemon-pepper wings my wife-to-be and I had at a cozy restaurant in the small New York state town where we lived in the early 1990s. These fat and juicy wings live up to my nostalgic hype.

7 p.m., Paramount Theatre

On my mural perambulation, I noticed a tour bus behind the Paramount Theatre, a thriving arts venue that’s undergoing a significant expansion. I check the theater’s website on my phone and see that tonight’s show is “Croce Plays Croce,” with musician A.J. Croce playing the songs of his father, Jim Croce, who died in a 1973 plane crash at age 30 when A.J. was not quite 2.

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Jim Croce was one of the first musicians whose songs I loved. Melancholy tunes like “Time In a Bottle” and “Operator (That’s Not the Way It Feels)” hit my dark, introspective side even as a wee lad. I never got to see Jim Croce play, so I figure I should seize the chance to hear his son perform his father’s songs, even if I only have 45 minutes from the 7 p.m. start time until I need to leave for the train.

I buy an aisle seat in the back row so I can leave unobtrusively mid-show. Almost as soon as I sit down I get a text from Amtrak saying my return train to Vergennes is running 20 minutes late. That buys me more Croce time.

A.J. Croce certainly knows his audience. “Well, did you get enough whoopie pies today?” he asks to cheers and laughs. “I got my fill. I’m good until next year.”

He opens with his father’s “You Don’t Mess Around with Jim,” the title track to the first album I ever bought. A.J.’s voice doesn’t have the gravelly warmth his father’s had, but he’s a good singer and his boogie-woogie piano playing is stellar. He performs songs that inspired his father and A.J. himself – “Ray Charles was my gateway artist,” he says – and some of his own material, including a soulful, Randy Newman-esque piano ballad.

He tells a story about how his father was at Fort Dix, New Jersey, in 1965, waiting to use the pay phone. “You probably know where this is going,” A.J. says, mentioning how his father overheard the devastating conversation a fellow soldier was having with the operator on the other end of the line.

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Then he plays “Operator,” Jim Croce’s song about a man trying desperately to reconnect against all hope with a lost love. My heart melts. It’s my favorite Jim Croce song. “Operator/Could you help me place this call?/’Cause I can’t read the number that you just gave me/There’s something in my eyes/You know it happens every time/I think about the love that I thought would save me.”

By the time he’s done, there’s something in my eyes, too.

7:52 p.m., Rutland Amtrak station

An ensuing text from Amtrak says the train is making up time and will only be 10 minutes late. I leave my seat for the three-minute walk to the station, arriving a minute before my originally scheduled departure time. Ten minutes after I get there another text says the train will be about 25 minutes late. I could have spent a little more time with A.J. Croce had Amtrak been more prompt letting me know about their lack of promptness.

8:23 p.m., leaving Rutland

The northbound train departs 27 minutes later than the original time, 10 minutes after its first rescheduled time, 20 minutes later than the second rescheduled time and five minutes before its third rescheduled time. Or something like that. Amtrak time is an elusive concept.

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On the ride back to Vergennes I think of my wisecrack this morning about how I might be the first person to have fun in Rutland. My contented fatigue as I relax in my seat tells me maybe I had too much fun in Rutland.

9:26 p.m., back in Vergennes

The train arrives 21 minutes late in Vergennes. My wife greets me near the station and we drive to the one downtown nightspot that’s still open, Bar Antidote, aka Low Bar, downstairs from the former Hired Hand taproom/restaurant on Green Street.

We enter a hallway leading to what feels like a speakeasy. Twenty feet from the eerily-quiet city we find a barroom brimming with loud music from Grateful Dead tribute band Dark Star Project and just-as-raucous conversation from revelers celebrating the waning moments of Vergennes’ Oktoberfest. The Hired Hand brewery still makes beer, so I get Hired Hand pilsners for my wife and I and we retreat to the quieter booths in the hallway.

I recount to my wife my fun day in Rutland and rue that I’m running out of Vermont downtowns to visit on the southbound train from Burlington. But wait, there’s the long-standing Vermonter line that leaves St. Albans and winds through all sorts of locales in eastern Vermont. Hmm … goals for next year ….

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If you go

Destinations visited for this article include:

  • Vergennes Laundry, 247 Main St., Vergennes. (802) 870-7257, www.vergenneslaundry.co
  • Ferrisburgh/Vergennes Amtrak station, 49 Park Lane, Ferrisburgh. www.amtrak.com/stations/vrn
  • Rutland Amtrak station, 25 Evelyn St., Rutland. www.amtrak.com/stations/rud
  • Vermont Farmers Market, Depot Street, Rutland. www.vtfarmersmarket.org
  • Whoopie Pie Festival, Rutland. www.rutlandwhoopiepiefest.com
  • The Rollin’ Rooster food truck, based in Pittsford. (802) 683-4124, www.therollinrooster.com
  • Speak Easy Café, 31 Center St., Rutland. (802) 855-8167, www.speakeasycafe.net
  • Rutland sculpture trail, locations throughout downtown. www.downtownrutland.com/sculptures
  • Hop ‘N Moose, 41 Center St., Rutland. (802) 775-7063, www.hopnmoose.com
  • Paramount Theatre, 30 Center St., Rutland. (802) 775-0903, www.paramountvt.org
  • Bar Antidote (Low Bar), 35 Green St., Vergennes. (802) 877-2555, www.barantidote.com

Contact Brent Hallenbeck at bhallenbeck@freepressmedia.com.



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Vermont high school playoff scores, results, stats for Thursday, March 5

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Vermont high school playoff scores, results, stats for Thursday, March 5


The 2025-2026 Vermont high school winter season has begun. See below for scores, schedules and game details (statistical leaders, game notes) from basketball, hockey, gymnastics, wrestling, Nordic/Alpine skiing and other winter sports.

TO REPORT SCORES

Coaches or team representatives are asked to report results ASAP after games by emailing sports@burlingtonfreepress.com. Please submit with a name/contact number.

Contact Alex Abrami at aabrami@freepressmedia.com. Follow him on X, formerly known as Twitter: @aabrami5.

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Contact Judith Altneu at JAltneu@usatodayco.com. Follow her on X, formerly known as Twitter: @Judith_Altneu.

THURSDAY’S H.S. PLAYOFF GAMES

D-III GIRLS BASKETBALL SEMIFINALS

At Barre Auditorium

No. 5 Vergennes (17-4) vs. No. 1 Hazen (18-2), 5:30 p.m.

No. 3 Oxbow (16-6) vs. No. 2 Windsor (16-6), 7:30 p.m.

Watch Vermont high school sports on NFHS Network

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D-I BOYS BASKETBALL QUARTERFINALS

Games at 7 p.m. unless noted

No. 8 Mount Mansfield (10-11) at No. 1 Rice Memorial (17-3)

No. 12 Essex (5-16) at No. 4 Rutland (15-6)

No. 7 Burr and Burton (13-8) at No. 2 South Burlington (15-5), 6 p.m.

No. 6 BFA-St. Albans (13-8) vs. No. 3 Burlington (15-5) at Colchester, 7:30 p.m.

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D-II GIRLS HOCKEY QUARTERFINALS

No. 8 Stowe (5-16) vs. No. 1 U-32 (13-6-1) at Kreitzberg Arena, 5 p.m.

(Subject to change)





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19 Vermont school budgets fail as education leaders debate need for reform

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19 Vermont school budgets fail as education leaders debate need for reform


MONTPELIER, Vt. (WCAX) – Most Vermont school budgets passed Tuesday, but 19 districts and supervisory unions saw their spending plans rejected — an uptick from the nine that failed in 2025, though well below the 29 that failed in 2024.

Some education leaders say the results show communities are largely supportive of their schools.

“We’re starting to kind of equalize out again towards the normal trend of passage of school budgets each year,” said Chelsea Meyers of the Vermont Superintendents Association.

Sue Ceglowski of the Vermont School Boards Association said the results send a clear message. “Vermont taxpayers support Vermont’s public schools,” she said.

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Meyers said the results also raise questions about the scope of education reform being considered in Montpelier. “If we are going to reform the system, it might not require sweeping broad changes as are being considered right now, but a more concise approach to consider that inequity,” she said.

But in districts where budgets failed, officials say structural changes are still needed. In Barre, where the budget failed, Barre Unified Union School District Board Chair Michael Boutin said the Legislature must, at a minimum, create a new funding formula. “We have to have that in order to avoid the huge increases and decreases — the huge increases that we’ve seen in the last couple years,” Boutin said.

He said the rise in school budgets is separate from why property owners are seeing sharp tax increases. The average state increase in school budgets is 4%, but the average property tax increase is 10%, driven by cost factors including health care. “There’s a complete disconnect, and that’s a product of the terrible system that we have in Vermont with our funding formula,” Boutin said.

Ceglowski says the state should address health care costs before moving forward with rapid education policy changes. “Addressing the rapid rise in the cost of school employees’ health benefits by ensuring a fair and balanced statewide bargaining process for those benefits,” she said.

The 19 districts that did not pass their budgets will need to draft new spending plans to present to voters, which often requires cuts. Twelve school districts are scheduled to vote at a later date.

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6 of the Quirkiest Towns in Vermont

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6 of the Quirkiest Towns in Vermont


Vermont is, for many visitors, the postcard-perfect New England state. A part of the United States since 1791, the first to join the Union after the Thirteen Original Colonies, Vermont has many unique, and sometimes quirky, features. The place has attracted artists and other creative geniuses, some of them decidedly eccentric, from its earliest days. The natural parts of Vermont, like the famous Lake Champlain, offer unusual points of interest for visitors and locals alike. With a state as rich in traveling attractions, it should be little wonder that some of them come with a quirk or two.

Montpelier

Summer Farmers Market in Montpelier, Vermont. Editorial credit: Phill Truckle / Shutterstock.com

Montpelier, while being Vermont’s charming capital, is the tiniest among all US state capitals with just around 8,000 residents. For comparison, the second-smallest, Pierre in South Dakota, has a population of about 14,000. Established in 1787, this historic town warmly welcomes visitors with a variety of landmarks, including the Vermont History Museum and the sprawling 200-acre Hubbard Park. The State House is also open to the public for tours. Just a short drive west, less than an hour away, lies Lake Champlain, one of the Northeast’s most beloved watersides.

The town’s name pays homage to Montpellier, a beautiful city in southern France. This naming reflected the high regard for France at the time, especially for their support during the US War of Independence. Interestingly, Montpelier has experienced its share of flooding, with significant damage occurring in the years 1927, 1992, and most recently in 2023.

Elmore

Lake Elmore State Part with beautiful autumn foliage and water reflections at Elmore, Vermont
Lake Elmore State Part with beautiful autumn foliage and water reflections at Elmore, Vermont

Elmore, a charming small town in Lamoille County with fewer than 900 residents, is a favorite spot for autumn leaf-peepers. Located north of Montpelier, this peaceful town has its own unique charm, including several local landmarks sharing the name ‘Elmore,’ which adds to its character. It’s important to note that Elmore town is separate from East Elmore. To the west, Elmore Mountain overlooks the area, while Elmore State Park lies just north of the town itself. Enjoying waterside beauty, Elmore Lake is often listed among Vermont’s most picturesque lakes, with its waters flowing into the Lamoille River through Elmore Pond Brook. Like Montpelier, Elmore is situated east of Lake Champlain. For those seeking a more bustling scene or a change of pace, the vibrant city of Burlington, just an hour’s drive west, makes for a perfect day trip or weekend getaway.

Stowe

Aerial view of Stowe Vermont and autumn colors.
Aerial view of Stowe Vermont and autumn colors.

Stowe, with a lively population of 5,300, is Vermont’s top spot for adrenaline seekers and the eccentrics among us, earning its reputation as the state’s premier ski and snowboard destination. The Stowe Mountain Resort proudly calls itself the “ski capital of the east”—that’s the eastern United States. Nestled near the breathtaking Mount Mansfield, Stowe offers more than just winter fun; warmer months bring plenty of activities like hiking and mountain biking in the beautiful Cady Hill Forest.

The town also has a rich history, being the home of Jake Burton Carpenter (1954-2019), the visionary behind Burton Snowboards and a trailblazer in making snowboarding an international sport. While some might have called him eccentric when he launched his company in 1977, today he’s celebrated as a true pioneer whose legacy keeps inspiring young snow sports enthusiasts, like those at Mount Mansfield Winter Academy, a special school dedicated to nurturing the next generation of champions.

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Manchester

View of the historic and colorful Manchester Village in Manchester, Vermont with tulips in bloom
View of the historic and colorful Manchester Village in Manchester, Vermont with tulips in bloom

Manchester, a town with 4,500 residents located in southwest Vermont, is popular among art and architecture enthusiasts. It features Hildene, the estate of Abraham Lincoln’s son Robert, which boasts an impressive Georgian Revival house and grounds. The town’s American Museum of Fly Fishing showcases numerous rods, flies, and related gear, attracting many superstitious anglers. Manchester is also home to Orvis, a renowned fishing and clothing company. The Southern Vermont Arts Center hosts exhibitions, and includes a sculpture garden and performance space. Nature lovers should visit Mount Equinox, west of town, or explore the Green Mountain National Forest to the south.

Eccentric fact: Jonathan Goldsmith, known for portraying “The World’s Most Interesting Man” in Dos Equis commercials, resides in Manchester. Stay quirky, my friends.

Brattleboro

Historic downtown of Brattleboro, Vermont.
Historic downtown of Brattleboro, Vermont. Image credit jenlo8 via Shutterstock

Brattleboro, with a population of 12,100, sits along the Connecticut River and features a variety of attractions and oddities. Located just west of New Hampshire—in which the Connecticut River forms the border—and just north of Massachusetts, the town is an ideal midpoint for exploring the wider New England region. Outdoor enthusiasts will appreciate Fort Dummer State Park, welcoming hikers, bikers, and campers alike. Among the more renowned eccentric figures in history, British writer Rudyard Kipling moved to Brattleboro after marrying a Vermont woman in 1892. Their home, Naulakha, references his birth and childhood in India. Kipling believed that Brattleboro’s conservative small-town culture created an

Woodstock

Snowy day at the farm in Woodstock.
Snowy day at the farm in Woodstock. Editorial credit: James Kirkikis / Shutterstock.com

Woodstock, a town with 3,000 residents located in upstate New York, is separate from the famous 1969 cultural event. This southeastern town attracts architecture enthusiasts, particularly for the First Congregational Church, built in 1807 and featuring a bell cast by American revolutionary Paul Revere, and the Norman Williams Public Library, completed in 1884. For outdoor activities, visitors can walk in Woodstock Town Forest, located south of the town, or enjoy panoramic views from the Marsh Billings Rockefeller National Historical Park, the only part of the US National Park system in Vermont besides the Appalachian Trail. Recently, Woodstock has modernized its infrastructure with digital technology, launching the “Wireless Woodstock” initiative in 2011, which provides free Wi-Fi across the entire town. It’s not quirky; it’s just cool.

Vermont’s Quirky Small Towns May Also Be Its Best

These small Vermont towns show the state’s sometimes quirky, but never boring character. Architecture fans will find unusual, beautiful examples state-wide. Montpelier is an oddly pint-sized capital with heavyweight history. Brattleboro has long attracted strange, sometimes brilliant types, whether foreign or domestic. Manchester is interesting enough for the World’s Most Interesting Man. And with abundant natural parks, the Green Mountains, and the majesty of Lake Elmore and Lake Champlain, the quirks of Vermont’s best features should attract even the most straight-laced visitors.



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