The Rye Line
Vermont. Five days. Two bases. One private farm you'll never forget.
Sleep in a historic inn. Blend your own rye on a 500-acre farm. Drive through peak foliage. Drink whiskey that's older than your career.
This Isn't a Tour Bus Trip
Vermont Whiskey Trail packages will drive you past the distilleries. We'll get you inside them — including one that doesn't open its doors to the public.
The Rye Line is a 5-day curated whiskey and foliage journey through Vermont's Middlebury corridor and the Woodstock-Quechee valley — two of the most beautiful and spirit-rich regions in New England that most American whiskey lovers don't know exist. You'll blend your own rye whiskey on a 500-acre farm where they grow the grain, harvest the oak, and age the barrels on-site. You'll taste spirits in a climate-neutral distillery, eat lunch overlooking a waterfall in hand-blown glassware made downstairs, and drive through peak foliage so vivid it looks AI-generated — except it's real.
Max group size: 10 people. No tour bus. No lanyard. No script.
Five Days. Two Valleys.A Lot of Rye.
Middlebury / Shoreham
“The Source”
Swift House Inn • 2 Nights
A restored 1814 Federal-style estate in the heart of Middlebury. Gardens, fireplaces, and a porch built for whiskey. Walking distance to downtown and the falls.
Fly into Burlington (BTV). Scenic 1-hour drive south through the Champlain Valley to Middlebury.
Check into Swift House Inn. Walk downtown Middlebury — the Otter Creek drops 18 feet into Middlebury Falls right in the center of town. Grab a coffee at Middlebury Chocolate overlooking the falls.
Afternoon: The Middlebury Tasting Trail warm-up. Three distilleries within 5 miles of each other:
- →Appalachian Gap Distillery — Small-batch gin, whiskey, and brandy in a barn off Route 116. The kind of place where the distiller pours your tasting.
- →Split Spirits — America's first climate-neutral certified distillery. Hopped whiskey made from Switchback Ale. Creemee-inspired liqueurs. Only available here.
- →Stonecutter Spirits — Heritage grain whiskey and gin. Beautiful tasting room on Exchange Street.
Evening: Welcome dinner at a farm-to-table restaurant in Middlebury. First pour of WhistlePig 10-Year to set the tone for the week.
This is the day that justifies the whole trip.
Morning: Drive 20 minutes to Shoreham. Private visit to WhistlePig Farm — 500 acres of rye fields, Vermont oak forests, a maple sugar bush, and a distillery built inside a 150-year-old renovated barn. This farm is not open to the public. You're getting in because we got you in.
Tour the distillery. See the custom copper pot stills. Walk the rye fields and aging barns. Meet the Kunekune pigs (they're part of the deal).
Late morning: The Blending Session. This is the signature experience. Using WhistlePig's barrel-finished ryes — Madeira, Sauternes, Port cask — you'll create your own custom blend under the guidance of the distilling team. Experiment with ratios. Taste as you go. When you're happy, you bottle it and take it home. Your whiskey. Your blend. Your label.
Lunch: Family-style on the farm property.
Afternoon: Scenic drive through Addison County during peak foliage. Optional stops at Lincoln Peak Vineyard for Vermont wine or Woodchuck Hard Cider for a palate change. The drive itself is the experience — roll the windows down, there's no rush.
Evening: Dinner in Middlebury. Free time to explore the town or sit on the Swift House porch with your first glass of something you blended yourself.
Woodstock / Quechee
“The Village”
The Woodstock Inn & Resort • 2 Nights
A landmark New England inn on Woodstock's village green, with a spa, tavern, and the kind of wraparound porch that makes you rethink your entire life. Listed on the National Register of Historic Places.
Morning: Check out of Swift House. Drive east through the Green Mountains to Quechee/Woodstock. This is roughly an hour, but during peak foliage this drive is a highlight — mountain passes, color everywhere, roadside farm stands.
Late morning: Quechee Gorge — Vermont's “Little Grand Canyon.” A 165-foot drop to the Ottauquechee River. Short accessible trails with dramatic views. The gorge bridge overlook is right off Route 4.
Lunch: The Mill at Simon Pearce — one of America's most romantic restaurants, overlooking a covered bridge and waterfall. Every glass on the table is hand-blown downstairs. After lunch, go downstairs and watch the glassblowers work. The Vermont Cheddar soup is mandatory.
Afternoon: Walk next door to the WhistlePig Whiskey Parlour — a speakeasy-style tasting room on the 2nd floor of the historic Parker House. Flight of WhistlePig expressions you won't find at your local store. Then walk the Quechee Covered Bridge for the full Vermont postcard moment.
Check into The Woodstock Inn & Resort.
Evening: Dinner at Richardson's Tavern — wood-paneled, fireside, classic Vermont. Cheddar fondue, venison, locally sourced everything. Named after the original 1793 tavern. The kind of place where you order an Old Fashioned and they know exactly what you mean.
Morning: Billings Farm & Museum — a working dairy farm since the 1870s on 400 acres. Cheddar-making demos, heritage breed animals, and a gorgeous property that looks like it was designed by someone who really loves Vermont. Or: Sugarbush Farm — hilltop farm with maple syrup tastings, aged cheddar samples, and panoramic views of the valley.
Late morning: Walk Woodstock village — the Green, the Middle Covered Bridge, boutique shops. Stop at Vermont Flannel for something cozy and Farmhouse Pottery for handmade ceramics.
Afternoon (choose your adventure):
- →SILO Distillery in Windsor — small-batch spirits in a gorgeous barn. Vodka, gin, whiskey, all Vermont grain.
- →Long Trail Brewery in Bridgewater — for the beer lovers in the group. Self-guided tour, riverside deck, live music seasonally.
- →Free time to hike, explore, or just sit on the Woodstock Inn porch and do nothing.
Evening: Farewell dinner — a private farm-to-table dinner paired with WhistlePig pours across the full lineup: PiggyBack 6-Year, the 10-Year Straight Rye, 12-Year Old World, 15-Year Estate Oak, and a surprise pour TBD. Guests taste their custom blends from Day 2 side by side. Toasts. Stories. The kind of night you'll talk about for years.
Breakfast at the Woodstock Inn.
Optional on the way to Burlington: Plymouth Artisan Cheese in Plymouth — America's oldest cheddar, originally founded by Calvin Coolidge's father in 1890. Pick up a wheel for the flight home.
Drive to Burlington (BTV). Fly home. You'll never drink a macro whiskey the same way again.
$2,499 Per Person
Here's everything that's in.
Included
- 4 nights in boutique hotels (Swift House Inn, Middlebury + The Woodstock Inn & Resort)
- All ground transportation between stops (private van — no bus)
- Private WhistlePig Farm tour, blending session, and take-home bottle of your custom blend
- WhistlePig Whiskey Parlour tasting in Quechee
- Middlebury Tasting Trail: tastings at 3 Vermont craft distilleries
- SILO Distillery or Long Trail Brewery tasting
- Welcome dinner in Middlebury with the group
- Farewell dinner with full WhistlePig lineup pairing
- Lunch at Simon Pearce overlooking the covered bridge
- All cultural entry fees — Billings Farm, Quechee Gorge, Sugarbush Farm
- Small group experience — max 10 people, no tour buses, no scripts
Not Included
- Flights to/from Burlington, VT (BTV) — book your own, we’ll share recommendations
- Individual meals beyond the 3 included (welcome dinner, Simon Pearce lunch, farewell dinner)
- Your whiskey purchases — you will buy bottles, budget accordingly
- Travel insurance (recommended)
Limited to 10 spots. Couples and solo travelers welcome. Double occupancy pricing — solo supplement available on request.
Where You're Sleeping
Swift House Inn
A restored 1814 Federal-style estate with gardens, fireplaces, and a porch made for evening pours. Walking distance to downtown Middlebury, the falls, and the tasting trail.
The inn where the whiskey tastes better because of where you’re sitting.
The Woodstock Inn & Resort
A landmark New England inn on the village green with a spa, Richardson’s Tavern, and a wraparound porch overlooking one of America’s prettiest small towns. Listed on the National Register of Historic Places since 1793.
The inn that makes you want to move to Vermont.
Questions You're Going to Ask
A lot — but this isn't a bachelor party with matching flasks. Every tasting is curated. You'll sip rye aged in Vermont oak barrels, blend your own whiskey on a working farm, and taste expressions most bars don't carry. There's also a working dairy farm, a glassblowing studio, a gorge, and enough fall foliage to fill your camera roll twice. You'll come home cultured AND well-poured.
No. You need to like whiskey and want to drink it somewhere beautiful. Local guides handle the knowledge. You handle the glass.
Yes. Solo travelers are welcome. Base price is per person, double occupancy — we'll pair you with another solo traveler of the same gender, or you can pay a solo supplement for your own room. Ask us for the solo rate.
Flights, individual meals (figure $20–35 per meal in Vermont), and your whiskey purchases. You will absolutely buy bottles — WhistlePig expressions at the source, small-batch spirits from the tasting trail. Budget $100–200 for bottles, more if you fall in love.
A reasonable daily food-and-drink spend beyond included meals is $50–80.
This isn't a hiking trip, but we walk. Expect 8,000–12,000 steps on active days. Quechee Gorge trails are accessible. Woodstock is flat and walkable. The WhistlePig farm has some terrain. Comfortable shoes are non-negotiable.
Book your own. Fly into Burlington (BTV) on October 9 and out on October 13. BTV has direct flights from most East Coast hubs and connecting service from everywhere else. We'll send flight recommendations and timing guidance after you book.
Vermont peak foliage typically runs late September through mid-October, and we've timed this trip to land right in the sweet spot. Nature doesn't guarantee anything, but early-to-mid October in the Middlebury-Woodstock corridor is historically peak.
It's an adult trip for people who appreciate craft whiskey, good food, and beautiful places. Some nights will go late. Some mornings will start slow. Nobody's keeping score and nobody's blowing a whistle. The itinerary has structure but plenty of free time to do your own thing.
$500 deposit is refundable until July 1, 2027. Balance due August 1, 2027. After August 1, no refunds — but you can transfer your spot to someone else.
Yes. The Rye Line — Winter Edition runs in February from Stowe, built around skiing, après whiskey, and the WhistlePig Pavilion at Spruce Peak.
Ten Spots. One Trip.Don't Overthink It.
October 9–13, 2027. Middlebury. Woodstock. Vermont.
$2,499 per person — all-in minus flights and your bottle habit
Ten people who actually care about what they're drinking. One week in Vermont.
The Rye Line is organized by Leave the Lanyard. All hotel bookings managed through Leave the Lanyard. Travel insurance recommended. Itinerary subject to minor adjustments based on local availability and weather.