MIDDLEBURY, CONNECTICUT
Enjoy the Day
With Us
A day trip designed around food, wine, shopping, relaxation, and unforgettable experiences — all in the heart of Middlebury, Connecticut.
THE EXPERIENCE
A Full Day of
Discovery
Spend the day discovering everything Middlebury has to offer. From brunch and boutique shopping to wine tastings and dinner under the lights, every stop is thoughtfully designed to turn a simple outing into an unforgettable escape.
YOUR CURATED ITINERARY
Your Day in Middlebury
11:00 AM
Brunch at Vyne
Start your day with brunch at Vyne — where elevated dining, handcrafted cocktails, and warm hospitality set the tone for the perfect escape.
1:00 PM
Explore & Shoppe
MIDDLEBURY FURNITURE • TAKE 5 AUDIO • THE SHOPPES
Start your day with brunch at Vyne — where elevated dining, handcrafted cocktails, and warm hospitality set the tone for the perfect escape.
3:30 PM
Wine Flights at Tranquillity Vineyard
Slow down with vineyard views and handcrafted wine flights at Tranquillity. Relax, reconnect, and enjoy the beauty of the countryside with every pour.
6:00 PM
Dinner & The Game at Brewbury
End the evening with incredible food, craft drinks, and a vibrant atmosphere at Brewbury — where casual comfort meets unforgettable flavor.
8:00 PM
Dessert & Cocktails at Vyne
Finish the night back at Vyne with dessert, cocktails, and late-night conversation in an atmosphere designed to make moments linger a little longer.
Times listed are simply suggestions — explore at your own pace and enjoy the experience in any order you’d like. The possibilities are endless.
Experience Middlebury Like Never Before
Romantic Escape
Perfect for date days, anniversaries, and unforgettable evenings.
Food & Wine Experience
Designed for food lovers, wine enthusiasts, and weekend explorers.
Girls Day Out
Shopping, wine flights, cocktails, brunch, and beautiful photo moments.
Free Parking
Everything Within Minutes
Perfect for Weekend Day Trips
Easy Drive from most areas in Connecticut & New York
PLAN YOUR DAY
Explore the Vyne Hospitality Group Locations
Most destinations are within minutes of one another.
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A Hidden Destination Worth Discovering
Just a short drive from New York, Westchester, Fairfield County, and beyond, Middlebury offers a different kind of Connecticut experience — sophisticated yet relaxed, luxurious yet welcoming.
Whether you're planning a spontaneous Saturday, a couples getaway, or simply looking for somewhere new to explore, VHG invites you to spend the day with us.
About Vyne Hospitality Group
VHG is a collection of hospitality, dining, retail, and lifestyle destinations created to bring people together through exceptional experiences. Rooted in generations of hospitality, every VHG destination is built around connection, quality, and unforgettable moments.
