8 Romantic Ways to Experience Middlebury, Vermont

Drinks at Jessica's Photo Courtesy: Caleb Kenna Photography
Photo Courtesy: Caleb Kenna Photography

Nestled in the heart of Vermont, Middlebury offers the perfect backdrop for a romantic New England getaway. Whether you are searching for outdoor adventure, culinary delights, or cozy activities, Middlebury offers a classic Vermont experience for guests looking to escape from the hustle and bustle of everyday life. Discover eight enchanting ways to explore Middlebury together at Swift House Inn. We’re here to help ensure you make memories that stand the test of time. 

Dinner at Jessica’s:

Looking for a special evening? Enjoy an exquisite dining experience at Swift House Inn’s very own restaurant, Jessica’s. Jessica’s sets the stage for a memorable evening with a carefully crafted menu filled with local ingredients complimented by our award-winning wine list. Be sure to end the night with a toast to your love. Cheers! 

steak dinner with wine flowers and cutlery
Photo Courtesy: Caleb Kenna Photography


Middlebury’s scenic landscape provides the ideal backdrop for a romantic outdoor adventure. Choose from the various hiking trails located near Middlebury to explore nature’s beauty. Whether you opt for a leisurely stroll or enjoy a more challenging trek, the stunning views and peaceful surroundings are sure to l bring you closer together. Check out the top 9 hiking trails near Middlebury, VT.

View from the top of My.Abe
View from the top of Mt. Abe

Wine Tasting at Lincoln Peak Vineyard:

Sip your way into romance at Lincoln Peak Vineyard, a picturesque vineyard that is just five minutes away from Swift House Inn. The perfect date location, sit back and sample the diverse flavors of Vermont wines while taking in the gorgeous views of the rolling hills and lush vineyards. The relaxed atmosphere and fine wine make for the perfect day spent. 

Wine Tasting Experience
Wine Tasting Experience || Photo Courtesy of Caleb Kenna Photography

Enjoy a Spa Day at Waterfalls Day Spa:

Treat yourselves to a spa day at Waterfalls Day Spa for ultimate relaxation. Rejuvenate, recharge, and reset as skilled therapists pamper you with massages or facials. The two of you will glow in love (literally). Be sure to request an appointment before you arrive!

Take a Sunset Drive:

Take a scenic drive through Middlebury’s picturesque countryside as the sun sets. The warm, golden hues will cast a romantic ray on your romantic Middlebury getaway. Pack a picnic basket, stop at a viewpoint, and share a special moment.

Dessert and Coffee Date:

Indulge your sweet tooth with a dessert and coffee date in Middlebury. Visit a local cafe or bakery and savor delicious treats and coffee in a cozy atmosphere. Downtown Middlebury is full of cafes to choose from. This simple, yet delightful experience is perfect for deepening your connection.

Stroll & Shop:

Explore the streets of downtown Middlebury together through charming boutiques and shops. You’re sure to find unique treasures, from handcrafted jewelry to local art, providing you with the perfect opportunity to pick up a little something special to remind you of your romantic New England getaway.  

Check out the Local Art Scene:

Middlebury has a vibrant local art scene, offering galleries and exhibitions to explore. Tap into your creative side together as you stroll through local art, which is always a romantic experience.

At Swift House Inn, we invite you to enjoy these romantic activities and create lasting memories with your loved one.

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