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Middlebury is classic Vermont. Set along the banks of the famed Otter Creek, you’ll find a quaint, yet vibrant downtown. Captivatingly located around a gorgeous public green, you’ll be happy to explore the many local shops, art galleries, and delicious restaurants. With miles of trails for hiking, biking, and skiing, Middelbury is a stunner from every vantage point. Welcome!
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Featured in Middlebury

The Hit List
The best of the best. The cream of the crop. The cow’s pajamas. These are the restaurants, hotels, and activities that you absolutely have to put into the planner when you visit. In fact, these are the places that are worth planning an entire visit around. Dive into our Hit List and let us know what you think!
Wine Time

Lincoln Peak Vineyards

There’s just something magical about the tasting room at Lincoln Peak Vineyards. A veritable oenophile oasis, the post and beam tasting room, pond-side setting, and sunlit rows of grape vines always leave us with a warm, cozy feeling inside. The absolutely delicious wines certainly only assist with that fuzzy, blissful feeling.
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Middlebury College

One of the nation's most prestigious colleges sporting one of the nation’s most beautiful campuses, Middlebury College is nothing short of an architectural dream. Local Tip: Be sure to visit Mead Chapel for stunning photos no matter what the season.
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Read More, Worry Less

Vermont Book Shop

Ahh…does anything beat the relaxing feel of an excellent bookstore? Middlebury’s Vermont Book Shop has been continuously operating since 1949 and locals and visitors alike have been enjoying this incredible, independent gem from jump street.
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Hike and Enjoy

Trails Around Middlebury

Part of the Middlebury Area Land Trust, Trails Around Middlebury (or TAM to locals) is a stunning trail system fully encircling the village of Middlebury with over 18 miles of quaint footpaths and vista-laden pathways. Get out and explore!
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Delicious + Entertaining

Fire & Ice

The only thing better than the food at Fire & Ice is quite possibly the vibe. Family-owned and operated since 1974, Fire & Ice is as much a museum as it is a local landmark. Each meal is an experience and we love taking it all in! Local Tip: If it hasn’t been completely sold out yet, get the Prime Rib.
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The Deep Dive

Middlebury Tips + FAQs

Drop-In Brewing Company
What are the local, must-see attractions or hot spots?
We’ve already mentioned above what a local favorite Fire & Ice is, but we feel it necessary to expound a little further. You ever go to one of those restaurants where you just know you’re always going to have not only a great meal, but just a good ol’ time? This is one of those spots. The servers are always friendly and actually seem like they genuinely enjoy being there and care about your meal. Plus, as we said earlier, the atmosphere is a total win. An actual motorboat, airplane propellors, fishing equipment, hundreds of black and white photographs, sports memorabilia - the deeper you look, the more you’ll find. The best way to sum it up might be a little controversial, but bear with us; it’s like imagine if TGI Fridays or a Bennigan’s actually had really great food and authenticity. Great atmosphere, delicious food, and a local family ownership that you just love to support. Local Tip: The attached Big Moose Pub is one of our favorite spots in town to grab a burger, a couple of pints, and watch a game. Just a great, great bar!

Speaking of places that are an absolute pleasure to support, you’ve got to swing by Drop In Brewery and meet brewmaster Steve Parkes! Steve is the founder of Drop In Brewery, a legitimate authority in the brewing industry, and couldn’t be a nicer guy. We love Drop In Brewery for their constantly rotating and envelope-pushing draft line, as well as for the classic favorites (we’re partial to Supernova IPA and Heart of Lothian). A stop in to their tasting room is always a great time and we consistently seem to walk out with at least a growler or two.
If you only had one night in town, where are you going for dinner?
If you couldn’t tell from our answer before, we’re pretty enamored with Fire & Ice. Every menu choice is solidly delicious, the prices are reasonable, the servers are friendly and helpful, and the drinks are cold and strong - what’s not to love?
We’re looking to splurge a little - where are the best digs in town?
Let’s just put this out there - you are really going to enjoy your stay at Swift House Inn. The attention to detail and effort that new owners Serena and Matthew are pouring into the inn is evident from the moment you walk through the doors. Each room is perfectly appointed and luxurious, while still ultimately cozy. We could go on and on about the level of service and hospitality that you’ll find here, but as we said, the bottom line is you’re really going to enjoy your stay. And don’t even get us started on the attached restaurant Jessica’s - the menu is amazing! Local Tip: The cocktails here are equally impressive - we fully support starting your stay with a libation or two.
Where should we go for unique, one-of-a-kind shopping?
Middlebury has some fantastic shopping options, and one of our favorites is Vermont’s Own Gifts & Goods. The secret is right there in the name; almost everything in the shop is from Vermont makers and producers. From Maple Syrups and candies, puzzles to woodcrafts, the items you’ll find here are incredibly well-made, unique, and undeniably Vermont-y. We love it.

Similarly, giving off that local feel, you should definitely find your way to The Stone Mill Public Market. With their basement housing the always delicious Mad Taco, a co-working space, stunning short-term rental units, and a curated shopping experience - Stone Mill has a little bit of everything. On the shopping side of things, we love the model that Stone Mill has built. By creating a community gathering space (coffee bar, gorgeous decks and patios), and bringing in multiple area makers and businesses and setting them up in almost mini-store/pods sections, they’ve constructed a really unique and fun experience.
We have our kids with us, where should we go with the entire family?
Whether you are a ‘horse person’ or not, a visit with the family to UVM Morgan Horse Farm is a great way to spend your afternoon. Open during the warmer months, be sure to get a guided tour of the picturesque stables and grounds.

Looking to burn off a little extra energy in an absolutely gorgeous setting? Take the kids and head just outside of town to the Robert Frost Interperative Trail. A gentle and beginner hiking experience, complete with wheelchair accessible boardwalk, this one mile looping trail goes through pastures and past beaver dams, and is interspersed with wonderful excerpts of Robert Frost poems. So what is the Robert Frost connection, you may ask? The Poet Laureate fell in love with - and lived in - nearby Ripton each summer for over 42 years. He also taught at Middlebury College’s Bread Loaf School of English during this time and would live and write in a small cabin close by to the trail. The area was a consistent source of inspiration and we know you’ll be similarly impressed!
We’re looking to start the day off right, breakfast recs? Is there a famous, local breakfast sandwich?
You’ve gotta go to Rosie’s! A family-style local favorite for more than five decades, Rosie’s is guaranteed to make you feel right at home! You’re going to have a winner with pretty much any selection, but if the morning is early and the stomach is grumbling, we’re always going with the Rosie’s Country Platter; Mckenzie Sausage Gravy and Homemade Biscuits, Two Eggs any style and Homefries (we like to add cheddar). We love their original, old-school slogan, “Good food, plenty of it, and it don’t take all day to get it.” Swoon.
We want to get out and breathe in some fresh air, what do you suggest we check out?
For Wintertime fun, the one-two combination of Rikert Outdoor Center and Middlebury Snow Bowl is a knockout. Rikert Outdoor is over 55km of trails built for cross country skiing (skate and classic), snowshoeing, and fatbikes. With a ski school and full service rental shop, the facilities and personnel are exceptional - possibly only eclipsed by the trails themselves. Meandering through old growth forests, stone walls, and rolling fields, this is quite the area to spend the day.

If downhill snow activities are more your speed, Middlebury Snow Bowl is just two minutes down the road. Owned and operated by Middebury College, this 600acre ski area is one of our favorite hidden gems. The lift lines are almost always short, the prices are reasonable, and the tree skiing here is just a ton of fun.

Another great way to get outdoors is to check out the TAM (Trails Around Middlebury). Part of the Middlebury Area Land Trust, TAM is a network of trails that circle all around downtown Middlebury and provide some excellent spots for scenic views. We’re especially fond of the Chipman Hill Loop, but be sure to take a look at the trail map as there are a ton of great options.
We’re coming up for a couples getaway - where should we go for a romantic dinner?
“New England food and wine. Elevated.” That’s the thought behind Jessica’s at Swift House, and we’re on board. To go into a little more detail, the ambiance at Jessica’s is impressive yet it manages to stay away from coming across at all as stuffy. The menu of course also shines, with creative and delicious options that are not only visually impressive, but are frequently excellent for sharing (an important date night factor). Between the setting, the service, the food, and the wine and cocktails, what’s not to love?
How about local music or entertainment?
While admittedly not boasting a huge music scene, there are still a few options to take in a local band or two. Our go-to is Two Brothers Tavern where you can catch some tunes on a Friday or Saturday night and belly up to the bar.

There is also the Town Hall Theater and the Opera Company of Middlebury which often have excellent performances and shows.

If you’re really hankering for a plethora of live music options, you’re only a stones-throw away from Burlington, which is just 35 minutes or so up Route 7.
We’re looking for something special for lunch - suggestions?
We have a hard time saying no to tacos for lunch and for this reason, when we’re in town we’ll be sure to hit up The Mad Taco. The tacos are tasty and fun, and if the weather is nice out, the patio is a great place to chow down.

Another excellent spot is Noonie’s Deli. A local favorite, Noonie’s is currently only offering take-out, but that’s not a problem for two reasons. One, the sandwiches are good enough that you’ll happily eat them wherever, and secondly, Noonie’s is directly across from Riverfront Park where you can find a bench or a table and take in the beautiful view of the falls.
After a long, fun day a cocktail sounds perfect! Where are we headed?
You won’t be surprised to find that we’re headed back to Jessica’s at Swift House! With the attention to detail that these folks put into all aspects of the customer experience, its no wonder that their cocktails are similarly excellent. You can’t go wrong with any of the choices, but we were particularly impressed with the smoothness and flavor of the Maple Manhattan.
We don’t want to be complete tourists - where are the locals going?
American Flatbread has five locations in Vermont and to be frank, we really dig all of them. They’re each quirky and unique and usually in historic settings - and the Middlebury Hearth is certainly no exception. Recently added is a gorgeous post and beam outdoor seating section where we love to grab a few pies and get a crew together to eat. Again, all excellent choices on the menu here, but our personal favorites are Punctuated Equillibriium and the Apple, Bacon, Cheddar. Amazing.
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Where To Stay in Middlebury

Where To Eat in Middlebury

What to Do in Middlebury

Middlebury Field Guides

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Chic Stays: Boutique Vermont Hotels

Our exclusive guide to the state’s most Instagram-able boutique hotels. Each blends captivating design with unique Vermont flair, delivering picture-perfect moments and stylish getaways.
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Green Mountain Lifestyle

Chic Stays: Boutique Vermont Hotels

Our exclusive guide to the state’s most Instagram-able boutique hotels. Each blends captivating design with unique Vermont flair, delivering picture-perfect moments and stylish getaways.
Sponsored by The Grafton Inn
Check It Out
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