Perfect for: Anniversaries • Honeymoons • Babymoons • Proposal Weekends • Birthday Celebrations • “Just Because” Getaways
A Three-Day Itinerary in Middlebury
Looking for the perfect romantic weekend in Vermont? As the owners of Swift House Inn—and a husband and wife who were married here ourselves—we’ve spent years discovering the little places, quiet moments, and memorable experiences that make Addison County one of New England’s most romantic destinations. Here’s exactly how we would spend three unforgettable days together.
Day One: Arrive, Unwind & Explore Downtown Middlebury
Your romantic Vermont getaway begins at Swift House Inn.
Check in at 3 p.m., settle into your room, and take a moment to enjoy your surroundings before heading out to explore. Every guestroom has its own personality, but some of our favorite romantic rooms include the Gladstone, Swift, Woodbury, Garden, and Addison rooms. Then again, we might be a little biased—we think they’re all romantic.
Once you’ve unpacked, stroll into downtown Middlebury. One of the pleasures of staying here is that the town is easily walkable. Cross the footbridge overlooking Otter Creek and pause to admire the dramatic waterfalls before browsing some of our favorite locally owned shops, including Vermont Book Shop, Vermont’s Own gift shop, and Flora cannabis boutique. Pick up a small souvenir—or perhaps a couple of pre-rolled joints—to remember your trip.
Return to the inn to freshen up before dinner.
An evening at Jessica’s is one of the highlights of any romantic weekend in Vermont. Over the years we’ve watched countless proposals, rehearsal dinners, anniversary celebrations, and first dates unfold in our dining rooms. Enjoy seasonal Vermont cuisine, an exceptional wine list, and the kind of intimate atmosphere that encourages lingering over dessert.
If you’re not quite ready for the evening to end, enjoy another cocktail in the bar or take a postprandial walk around nearby Chipman Hill. If you’d rather stay close to the inn, there are many amenities to choose from: unwind with a steam, dry sauna, or refreshing shower before settling in for a restful night’s sleep.
Day Two: Discover the Best of Addison County
Wake to a hearty breakfast at the inn, complete with fresh coffee, eggs cooked to order, pancakes, bacon, omelets, and warm hospitality.
Today is all about discovering what makes Addison County so special.
Visit a Vermont Farm
One of our favorite things about this region is its thriving agricultural community, and every season offers something different.
In early spring, visit a local sugarhouse to watch maple sap transformed into syrup while chatting with the families who have been making maple for generations.
Summer brings berry picking, overflowing farm stands, and beautiful country drives through fertile farmland.
Autumn means apple orchards, crisp mountain air, and harvest festivals. If you find yourself with more apples than you can carry home, we’ll happily turn them into pies or horse treats.
Winter has its own quiet charm, but limited farm tourism opportunities. You may be able to visit Bridport Creamery for fresh Vermont cheese or stop by Champlain Valley Creamery to experience another side of the state’s celebrated artisan food culture.
One piece of local advice: whenever you pass a farm stand, stop. Most operate on the honor system, and they offer some of the freshest produce, flowers, baked goods, and local treasures you’ll find anywhere.
For lunch, assemble a picnic from one of Middlebury’s markets or general stores and head somewhere scenic.
If it’s warm outside, cool off at one of the area’s swimming holes or relax beside Lake Champlain. If you’re visiting during cooler months, spend an hour beside one of the inn’s fireplaces with a good book and something warm to drink.
Take a Scenic Drive
In the afternoon, choose your own adventure.
Drive west toward Addison and the shores of Lake Champlain, where expansive lake views and the distant Adirondack Mountains create one of Vermont’s most beautiful landscapes.
Explore the Green Mountains
Or head east on scenic Route 125 into the Green Mountains. Stop near the Bread Loaf campus for a picnic before exploring some of the area’s wonderful hiking trails. The Robert Frost Interpretive Trail offers an easy walk through the forest, while Burnt Hill Trail rewards adventurous hikers with remarkable mushroom diversity during the wetter months. Texas Falls is another favorite, where spectacular waterfalls are only a short walk from the parking area.
Wine Tasting at Lincoln Peak Vineyard
After a day outdoors, continue north to Bristol for dinner at The Tillerman, one of our favorite restaurants in the region. Before your reservation, wander through Bristol’s charming downtown, exploring its record store, antique shops, vintage boutiques, and locally owned businesses. On your way there, consider stopping at Lincoln Peak Vineyard for a wine tasting, which is incredibly under three miles from the Inn.
Return to Swift House Inn for one last cocktail before turning in for the evening.
Day Three: A Slow Vermont Morning
Your final morning should be unhurried.
If you’re staying at the inn, linger over another complimentary breakfast. If you’d like to experience another side of Middlebury, grab one of Haymaker Bun Company’s famous sticky buns or enjoy beautifully crafted coffee drinks at little seed COFFEE ROASTERS.
These are the places where you’ll find professors, students, artists, and longtime locals beginning their day. You may even spot bestselling novelist Chris Bohjalian or author Jay Parini working quietly over coffee. If you do, admire from a respectful distance.
If your schedule allows, extend your stay just one more day.
Take a couples’ DJ class or kimchi-making class at Swift House Inn, join a guided fly-fishing experience, or begin your Saturday morning with complimentary yoga at the inn.
And if you’re looking for another memorable dinner before heading home, we also recommend Starry Night Café, Tourterelle, or Crooked Ladle.
Why Couples Return to Swift House Inn
The most romantic weekends aren’t built around checking attractions off a list.
They’re made from slow breakfasts, long conversations over dinner, quiet walks, beautiful landscapes, and the feeling that, for a few days, time has slowed down.
That’s what we love most about Addison County.
Whether you’re celebrating an anniversary, planning a surprise getaway, or simply making time for each other, we hope your romantic weekend in Vermont becomes the first of many visits.
Serena’s Romantic Weekend Survival Kit:
- Permission to leave your phones in the room
- An ice bucket – just ask for one
- Champagne – available as an add-on during booking
- Chocolate-covered strawberries – also available as an add-on
- Waffle robes – in every room
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