HONEYPOT Guide to Holiday Activities in Southern Vermont
The Holidays just feel different in our little nook of Southern Vermont than they do in the big city or the burbs. Our first snowfall often happens in November, and by the time Christmas rolls around, the landscape shimmers like a snow globe that’s come to life. Snow crunches underfoot, warm cider fills your cup, and each village glows with festive magic. From Instagram-worthy sleigh rides under the stars to bustling bazaars, here’s your locals’ guide to the season’s best.
Location: Weston, Vermont
Distance from Honeypot Farmhouse: Approximately 1 mile
Address: 657 Main Street, Weston, VT 05161
Active Dates: Year-round, with Holiday events from late November to December.
The most famous thing about our tiny town of Weston is The Vermont Country Store. Over the years it’s grown into a catalog staple (and e-comm giant) of country living, but it all started right here in Weston in this actual shop.
Step inside, and time seems to pause—carols drift through the air, floors creak underfoot, and every shelf holds something with a story: hand-labeled preserves, cast-iron pans, and vintage ornaments. Founded in 1946 by Vrest Orton, who modeled it after the general stores of his childhood, the place still runs as a family business today. During the holidays, expect hand-dipped candles, house-baked pies, and the occasional visit from Santa.
Nearby Pit-stop: Given how close this is to Honeypot, it’s not as if you can’t just pop back to the house after a country store outing. But while you’re there, you might as well stop at Mildred’s Table. Over the years, Mildred’s has had quite a few incarnations, and frankly, while all have been different, they have all been worthwhile. This latest iteration, which just opened in 2025, serves classic home-cooked American Fare. We’re a sucker for the grilled cheese with fries. And don’t tell your personal trainer, but we suggest washing it down with a maple milkshake.
Location: Weston, Vermont
Distance from Honeypot Farmhouse: Approximately 1 mile
Address: Village Green, Weston, VT (with events throughout town)
Active Dates: Typically the first Saturday in December (Check website for details.)
Christmas in Weston is one of those small-town Vermont traditions that captures the true spirit of the season. For one Saturday each December, our little village turns into a snow-dusted postcard. There’s live music spilling from the church, kids decorating cookies, horses clip-clopping down Main Street, and the smell of hot cocoa and wood smoke in the air.
The day begins around the Village Green, where local shops open their doors with special treats and holiday sales. Santa and Mrs. Claus make their grand entrance (usually by horse-drawn wagon) greeting kids at The Little School. Over at the Farrar-Mansur Museum, you’ll find crafts, story time, and enough sugar cookies to keep everyone smiling. Carolers from the Burr & Burton Academy fill the air with classic tunes, and as evening falls, the whole town gathers for the lighting of the tree and a small fireworks show to close out the night.
It’s not just festive, it’s pure Weston: charming, heartfelt, and community-run. Every bit of the event is organized by local volunteers, with proceeds supporting The Little School and the Weston Volunteer Fire Department. It’s the kind of Holiday celebration that reminds you why small towns do Christmas best.
Nearby Pit-stop: As we just noted, given that you’re barely a mile from Honeypot, you could stroll when you’ve had your fill of cheer, but if you’re looking to linger, stop in at Mildred’s Table for lunch. Note that at the time of writing, they are not open for dinner.
Location: Weston, Vermont
Distance from Honeypot Farmhouse: Approximately 1 mile
Address: Temporarily at Walker Farm, 705 Main Street, Weston, VT while the Weston Playhouse at 8 Park St, Weston, VT 05161 undergoes repairs.
Active Dates: Friday and Saturday after Thanksgiving, and then “Christmas in July” usually the last Saturday of the month. (Check Facebook for details.)
If Weston’s Christmas in early December seems cozy, the Weston Christmas Bazaar is its bustling warm-up act. Held in late November, where locals and visitors gather to kick off the season with handmade treasures, festive food, and community cheer.
The bazaar features over 50 artisans selling holiday gifts, wreaths, decorations, local foodstuffs, jewelry, and artwork. Because the Weston Playhouse has been under repair from the 2023 floods, the event has moved to the Walker Farm Theater, just down the road. There’s no admission fee; it’s free to browse and shop.
Over the years, the bazaar has grown more than a simple craft fair. It now supports Weston’s arts and culture: proceeds help fund the restoration of the Weston Playhouse. Local food vendors line up inside offering smoked meats and yummy treats. There’s also a raffle; past prizes include gift certificates, vendor-donated items, and more.
It’s not just a shopping spree, it’s the moment when Weston flips the switch into holiday mode. Strings of lights, chatter in cozy corners, and the warmth of small-town Vermont help to kick off the Holiday season.
Nearby Pit-stop: There are typically food trucks parked outside, but see above for some other nearby options.
Location: Londonderry, Vermont
Distance from Honeypot Farmhouse: Approximately 8 miles
Address: 825 Route 11, Londonderry, VT 05148
Active Dates: Mid-December through February, weather permitting.
Taylor Farm, a working dairy operation since the 1800s, becomes a snowbound retreat each winter. Enjoy sleigh rides that wind through open meadows and forest paths, while keeping cozy beneath thick wool blankets and the peaceful clomping of hooves. Midway, the sleigh stops at a rustic warming hut, where guests toast marshmallows over an open fire and sip hot chocolate.
The full experience lasts between 45 minutes and an hour. Afterward, you can browse the farm store stocked with raw-milk cheeses, maple syrup, and handmade goods — all crafted with care and heritage-breed cows.
Rides are private and reserved for groups of 2–10, priced around $350 plus tax and gratuity (but call to confirm). Reservations are required and must be made by calling 802-824-5690. Rides operate daily, weather permitting.
Visitors can still enjoy a similar experience during non-winter months. Taylor Farm offers hay rides during most of the rest of the year. Check their website for details.
Nearby Pit-stop: After your sleigh ride, swing by The New American Grill on your way back to Honeypot for a Black & Bleu Burger, “Jerk Grouper” (a sleeper menu item) or a Half Rack O’ Ribs over some live tunes from a Grateful Dead cover band, or order to-go and enjoy your grub back at the house.
Location: Manchester, Vermont
Distance from Honeypot Farmhouse: Approximately 25 miles
Address: 1005 Hildene Road, Manchester, VT 05254
Active Dates: Late November through early January.
Hildene Mansion, the historic Lincoln family home (Yes, those Lincolns, but not that Lincoln!), dazzles visitors with its elegant holiday decorations. The mansion is adorned with garlands, twinkling lights, and beautifully decorated Christmas trees.
Guests can take a self-guided or docent-led tour of the home, learning about its history and holiday traditions of the early 1900s. The estate’s gardens and walking trails offer scenic views, especially at dusk when the lights glow against the snow-covered landscape.
Special events like wreath-making workshops and seasonal concerts take place throughout December. The museum shop offers unique holiday gifts, including books, candles, and artisanal goods.
Free parking is available on-site. Light refreshments are available at the visitor center. Admission is $23 per adult, $6 for children under 16, and free for children under 5.
Nearby Pit-stop: If you’re looking for our favorite nearby sips and bites, The Crooked Ram is our go-to. A stylish, modern tavern offering a rotating menu of seasonal small plates, wood-fired dishes, and a carefully curated selection of craft beer and natural wines. Get the Ram’s Board! For something more-casual, swing by Haig’s Sports Bar for craft beer and bites. No matter where you go, check out Mother Myrick’s for some sweet treats on your way home. (We love the Lemon Lulu Cake, dark chocolate covered orange peel, and their signature Buttercrunch—all made on-site!)
Location: Peru, Vermont
Distance from Honeypot Farmhouse: Approximately 11 miles
Address: 179-15 Hapgood Pond Rd, Peru, VT 05152
Active Dates: Mid-December through early March, weather permitting
Located in the center of Peru, this small outdoor rink comes together each winter thanks to local volunteers. It’s simple, low-key, and exactly what you’d expect in a Vermont mountain town: skates scraping, snow falling, and neighbors pitching in to keep the ice smooth.
Unlike many “unsanctioned” ice rinks, this one isn’t set on a frozen pond, so you’re not skating over potentially-dangerous open water. Still, it is unattended, so glide with care and be respectful of the neighbors who make it possible. Skating here is free, unstructured, and wonderfully nostalgic; just the sound of blades cutting into the ice beneath the clear Winter sky.
If the weather doesn’t cooperate, or you’d rather skate somewhere a bit more official, Riley Rink at Hunter Park in Manchester is exactly what you’re looking for. It’s indoors, climate-controlled, and still full of small-town charm—complete with Holiday music and hot cocoa waiting by the concession stand.
Nearby Pit-stop: When the chill sets in at the Peru Ice Rink, head right across the street to JJ Hapgood General Store & Eatery for their wood-fired pizza—crisp, smoky, and just what a winter day calls for. Grab a slice, a cider, and a seat by the window to watch the snow fall over Peru’s tiny main street.
Location: Woodstock, Vermont
Distance from Honeypot Farmhouse: Approximately 32 miles
Address: 69 Old River Road, Woodstock, VT 05091
Active Dates: On and off in December and into January. Check website for details.
Travel to a Victorian Christmas past as you explore the farm’s authentically decorated farmhouse parlor, festive holiday tree, and historic barn. You can try your hand at dipping your own candle and making mini mince pies to take home. Warm up by the outdoor fire pits with hot cocoa and spiced cider, or take a peaceful snowshoe, hike, or cross-country ski along the Ottauquechee River, weather permitting.
On the farm, you can meet the resident Jersey cows, draft horses, chickens, sheep, and goats. Be sure to take a horse-drawn sleigh or wagon ride through the picturesque pastures, weather permitting, on select days from 11:00AM to 3:00PM. Public sleigh rides are an additional fee.
The Museum Gift Shop is a great spot for holiday shopping, with a solid selection of local Vermont gifts, specialty foods, and, of course, Billings Farm cheddar.
Admission is $21 per adult, $12 for children ages 4-15, and free for children under 4. We recommend purchasing advance tickets online to expedite the check-in process. You don’t need to pay admission to shop in the store.
Nearby Pit-stop: If you’re in the mood for a sit-down meal, Worthy Kitchen in Woodstock is one of the most underrated spots in all of Southern Vermont and offers counter service featuring gourmet, farm-to-table New American eats. The “OG fried chicken sandwich” is bonkers and their selection of local craft brews is next-level and in constant rotation. For all y’all New Yorkers out there, fun fact—Worthy Kitchen has the same owners as Spring Lounge and Blind Tiger Ale House.
Location: Woodstock, Vermont
Distance from Honeypot Farmhouse: Approximately 35 miles
Address: Village Green & surrounding venues, Woodstock, VT
Active Dates: December 12–14, 2025
Each December, Woodstock transforms into a scene that feels straight from your favorite Hallmark movie. Now in its fourth decade, Wassail Weekend was first celebrated in 1983 as a way to bring the community together during the darkest days of Winter. The name comes from the Old English toast “was hál” (which means to “be in good health”), and the weekend still carries that spirit of joy, warmth, and good fortune.
The highlight is the Wassail Parade, founded in the late 1980s by Antoinette Matlins, Paul Kendall, and a dedicated group of locals. Horses in jingling harnesses, riders in olde time attires, and decorated wagons circle the Village Green, with townsfolk and visitors lining the streets to cheer them on. Beyond the parade, the weekend overflows with traditions: bonfires and caroling, horse-drawn carriage rides, artisan fairs under the Middle Covered Bridge, and “Christmas at the Farm” at Billings Farm & Museum.
Over time, Wassail Weekend has grown into one of Vermont’s most cherished holiday celebrations with equal parts history, festivity, and small-town magic.
Nearby Pit-stop: We already mentioned Worthy Kitchen as a great stop, but we’d be remiss if we didn’t also mention Long Trail Brewery on your way out of town as another great option. You can’t go wrong with a classic “Long Trail Ale” or the seasonal “Hibernator” Scotch Ale, and we’re suckers for their fried pickles and hot soft pretzel with beer cheese.
Enjoy your Holiday season in Southern Vermont!
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Welcome to Honeypot Farmhouse— Your family's year-round VT retreat. We're under 10 miles from Okemo & Magic, 14 miles from Bromley, & less than 35 miles from Stratton, Mt Snow & Killington. We just renovated our 1850s home to be a balance of modern and cozy; where we—and you—will never want to leave. Come for a fun-filled weekend on the mountains skiing or a relaxing getaway in nature. End your day curled up by the fire in our cozy Great Room or over a glass of wine in our open-concept kitchen