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Some places to pop the question: consider writing the next chapter of your love story in Southern Vermont

By Danielle M. Crosier, Vermont Country Magazine.

We love the things we love for what they are.” — Robert Frost

Planning a marriage proposal is an entirely personal event. It is a reflection of who you are, how well you know your significant other, and how you want to spend your time together. It holds meaning, and is symbolic.

Although there are many special ideas for popping the question, here are a few special ideas themed on the charm and whimsy of Southern Vermont.

Something old, something new

McWayne Jewelers in Manchester offers a fine selection of estate rings, antique and vintage.
Main Street Antiques in Bennington hosts 16 different vendors, many of whom offer estate jewelry.

Looking for an engagement ring? Take a road trip through Southern Vermont and browse through the numerous antique and estate jewelers.

Or, work with one of the region’s talented fine jewelers to make something completely new, designed especially for you.

The symbolism of a vintage or antique engagement ring is that it has already experienced at least one love story, if not more. A vintage ring, for example, is typically older than 20 years — while an antique ring has a history of 100 or more years. An estate ring simply means that the ring is secondhand, regardless of age or wear.

“We’ve been here since 1948,” said Timothy Powden, graduate gemologist, seventh-generation jeweler, and owner of McWayne’s Jewelers in Manchester, now in its 75th anniversary year.

McWayne Jewelers in Manchester offers visitors a selection of over 300 estate pieces.

“Our estate jewelry is sourced from our customers,” said Powden of the shop’s extensive collection of vintage and antique rings. McWayne’s Jewelers also offers new, one-of-a kind designs. “We do custom work. We can build anything. It’s a question of the pocketbook and the imagination. Those are, you know, the only two limiting factors.”

When asked if he possibly has a favorite engagement story, Powden can’t pick.

“It’s just the element of surprise, you know? When a guy makes a plan, has her taste in mind — has either a custom piece made or finds something that’s right up the alley of what she’d be looking for — and pops the question.”

Timothy Powden

Trends come and trends go, and the personal nature of jewelry is a reflection of the owner. So, proposing with a diamond engagement ring may not be exactly what you’re after.

Main Street Antiques in Bennington, which hosts 16 different dealers, has cases of estate jewelry throughout the store. Shauna Del Prete, managing partner, knows a lot about the history of jewelry as a means of proposal.

“People aren’t just looking for diamonds anymore. No, no. It’s opals. It’s sapphires. It’s pearls. It’s anything they like. And, you know what? Not until this last century was the diamond an engagement ring,” she said. “You either got what your birthstone was or something from the groom’s family — a jewel that was set into a ring. It was rarely a diamond. Sometimes they didn’t even have a ring; sometimes it was a lavalier.”

The setting to start the next chapter in your personal love story

There’s something incredibly intimate about a bookstore, and choosing to propose in one of Southern Vermont’s eclectic independent bookstores might just help turn the page to the start of the next chapter in your love story.

Whether it’s tucking a “will you marry me?” bookmark inside the pages of a special book or arranging to hide your personal love story among the shelves, Southern Vermont’s booksellers are sure to welcome a bookshop proposal.

Scott Austin, director of operations and co-owner of Northshire Bookstore in Manchester, agreed.

“We fully support the creativity, magic, and spontaneity involved in asking that special someone that special question, and we’re happy to even be a small part of the lifelong memories created by our guests.”

The selection of independent bookshops in Southern Vermont is as varied as their contents.

When it comes to bookstores, Southern Vermont offers a variety of possible locations.

“We at Everyone’s Books believe there’s nowhere better to start your story together than your local bookstore,” said Red Durkin, the new owner of Everyone’s Books.

“Whether it’s the smell of the paper and ink emanating from the seemingly endless supply of books, or the sounds of the old hardwood floors that lead to the various nooks and crannies, it’s no surprise that some lucky folks have and will continue to choose indie bookstores such as ours as their proposal venue,” agreed Austin.

Everyone’s Books in Brattleboro is just one of many unique and quirky bookstores in Southern Vermont.

Everyone’s Books in Brattleboro, which offers a spectacularly diverse mix of fiction and nonfiction books, stickers, posters, clothing, and more, focuses its efforts on bringing social activism, environmentalism, and sustainability to the experience.

To have and to hold from this day forward — the setting of a proposal at Bartleby’s Books in Wilmington.

Bartleby’s Books in Wilmington, in the sweet little downtown shopping and dining area of Wilmington, specializes in quirky cards, fun games, curios, and books in a wide range of genres. Upstairs, lies a quaint (and most comfortable) seating area, more books, and a gallery that hosts the works of local artists.

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The setting of Southern Vermont is the idea location for a romantic proposal.

The Bennington Bookshop in Bennington, having established itself in 1928, has a claim to fame as the oldest independent bookstore in the state. The shop profiles bestsellers, reference books, comic and graphic novels, game and activity books, and cards.

Northshire Bookstore in Manchester is not just a bookstore, although they pride themselves on their massive, multi-story collection of over 300,000 books (and access to over 10 million books online). The family owned and operated business also sells local and global artisan-made crafts, stationary, vinyl records, rare used books and reference materials, and hosts author events and reading groups.

Pining for the apple of your eye on the Robert Frost Trail

The sign for Poetry Trail is posted at the base of an old gnarled stump of an apple tree that once stood behind Robert Frost’s stone house in Shaftsbury. Danielle M. Crosier — Vermont Country Magazine. .jpeg
An estate ring rests in a stained glass box on the Robert Frost Trail. Danielle M. Crosier — Vermont Country Magazine. 

Robert Frost planted two types of trees at his estate in South Shaftsbury: fruit-bearing apple trees and red pines.

Robert Frost, Vermont’s first poet laureate, lived for a time in the stone house in South Shaftsbury where he aspired to become an apple farmer. While his ambitions of farming were never fully realized, remnants of his apple trees remain.

Just behind his house, the gnarled and gray stump of one of these rises above the grassy field. Below it, rests a sign that reads, “Poetry Trail,” with an arrow pointing toward a path, nestled among a grove of trees. Wandering through this path, visitors will be able to read a few selected fragments of Frost’s poems. But this is not the Robert Frost Trail.

The entrance to the 2-mile long Robert Frost Trail lies just to the left of the entrance to the estate. It has its own free parking, is open year-round, and the entrance to the trail is clearly marked. At the start of the trail, hikers will pass beneath and alongside the few remaining living apple trees and the red pines planted by Frost and his son, Carol.

The trail meanders gently through the woods toward Lake Paran, offering hikers stunning views along the way. There are numerous sites suitable for a proposal, including a wooden bridge with benches, which is near the halfway point of the hike.

The trail is posted with signs and, echoing the sentiments of his famous poem, it has two paths that diverge in the yellow wood. Hikers need not fear, as both paths lead to the same destination — the north shore of Lake Paran.

“Whose woods these are I think I know. His house is in the village, though; He will not see me stopping here, To watch his woods fill up with snow,” Frost wrote while living at the stone house in Shaftsbury. “The woods are lovely, dark and deep. But I have promises to keep, and miles to go before I sleep.”

A romantic at heart, Frost would no doubt be pleased to know that love still blossoms in the woods behind his beloved home. “Suddenly, quietly, you realize that — from this moment forth — you will no longer walk through this life alone. Like a new sun this awareness arises within you, freeing you from fear, opening your life. It is the beginning of love, and the end of all that came before,” he wrote.

No cold feet at Riley Rink

For-ice-hockey-fans-the-game-has-been-compared-to-love-—-its-messy-its-emotional-its-intense-and-its-surprising.-Propose-at-a-pickup-game-on-the-ice-at-Riley-Rink-in-Manchester.
For ice hockey fans, the game has been compared to love — its messy, its emotional, its intense, and its surprising. Propose at a pickup game, on the ice at Riley Rink in Manchester. Danielle M. Crosier — Vermont Country Magazine.

Riley Rink at Hunter Park in Manchester is part of the larger Northshire Civic Center facility.

“We have the rink, which is also a turf complex during the spring and then an event venue during the summer and fall before we put the ice in. But, on the other side of the property is the Hunter Park Fields, and that actually is a rentable wedding venue,” explained Joe Ferguson, programs coordinator at the rink. “It’s just a few minutes walk from the rink.”

It is home to the National Hockey Association’s Northshire Bulldogs. It’s also the region’s only Olympic-sized ice rink.

“I feel like there are a lot of couples that are into hockey here. So, if they were to play pickup hockey or something,” he said, “Any of our leagues or pickup programs would be willing to help get something like that sorted on the ice.”

In the holiday season, he suggests proposing during a public skate.

“The place is just packed with people,” Ferguson continued. “There are a lot of out-of-staters that come, especially when the mountains don’t have snow. People will come down here to do something fun.

“If someone reached out, we could at least give them a schedule of when there’s going to be ice time available — if they wanted to do a private rental or if they wanted to come to a public skate. When people do public skate, center ice is pretty much always open — so, if they want to propose on the Bulldog, you know …

On-ice proposals have to happen between the second week of October and the first week of March, Ferguson said. “After that, it’s just turf or event space.”

If Southern Vermont holds meaning for you and your intended, reach out to some of the local business owners — especially if the location has personal significance to your relationship or aspirations.

They’re sure to welcome you.


Danielle Crosier is a landlocked mermaid who found her way to Vermont by accident. She is a wife and mother, a former technical writer (10 years), former educator (19 years), and glass artisan with a background in marketing and strategic management. Her interests, though, lie mainly in studying and understanding systems and improving the lives of those around her. She also loves spending time with her precious children and their significant others, organizing, learning about social geography, creative endeavors, experimenting with various cuisines, and exploring the world around her. 

Vermont Country magazine

Vermont Country has a hyperlocal focus on the Green Mountain lifestyle, its personalities, events, attractions and culture. The magazine appears six times a year, designed to complement the state and four-season living. VtCo magazine is a Southern Vermont publication of Vermont News & Media.

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