The Shire Woodstock

Woodstock, Vermont

If you’ve been dreaming about a getaway to Woodstock, Vermont, let me introduce you to a little gem called The Shire Woodstock. This charming riverside hotel is nestled right in the heart of one of New England’s most picturesque towns, and it’s the perfect spot for a relaxing weekend escape, a romantic trip, or even a basecamp for exploring Vermont’s outdoorsy side. I recently stayed at The Shire on my solo 3-night Vermont trip. Let me tell you all about my stay.

Location

The Shire is located right on the Ottauquechee River, and you’re walking distance to downtown Woodstock, where cute boutiques, cozy cafes, and classic New England architecture are around every turn. It’s also convenient if you’re planning to visit Billings Farm & Museum, Marsh-Billings-Rockefeller National Historical Park, or take a scenic drive through the Green Mountains. For skiers or snowboarders, Killington Resort and Suicide Six Ski Area are both an easy drive away.

First impression

The river flowing right by the property gives a peaceful, laid-back vibe. The building itself is classic Vermont: think charming inn-style with a modern twist.

Let me show you around my room.

I was in a building next to the main hotel. I love that it felt like an apartment building.

 I stayed in a

River King

The rooms at The Shire are simple, but super cozy and clean. I stayed in a River King Room, and waking up to the view of the river right in my backyard and sitting outside with a cup of coffee in hand was heavenly.

The rooms have that rustic-chic Vermont feel—unique furniture, warm lighting, and big windows to soak in the view. I felt like I was staying in a friend’s house instead of a hotel.

Two windows and the glass French door allowed natural light to flood the room.

 The room had a comfortable king bed and the pillows were amazing. There was a small flat-screen tv that played local and cable channels. The Wi-Fi worked really well and I never had any problems with it.

There were 2 sitting areas in the room… a cozy loveseat and a beautiful rocking chair.  They were nice spots to relax.

The room had a refrigerator so you can store snacks and beverages, which was perfect because I had accumulated lots of cheese during my trip.

My bathroom was large and had lots of water pressure. The towels were fluffy and there was lots of space on the vanity.

I loved the Adirondack chairs right outside my door. It was the perfect spot to relax and listen to the river!

In the hallway, right outside my room was a Keurig machine with a variety of Green Mountain coffee and a microwave. It was so convenient!

Ambiance

One thing I loved about The Shire was how quiet and relaxing it felt. There’s no hustle and bustle here—just a calm, peaceful place where you can really unplug. It’s the kind of spot where you grab a book, sip some hot cocoa, and watch the snow fall outside your window (or the leaves change if you’re there in the fall)

The personal touches make a hotel memorable. There were many cute decorations that gave a homey Vermont feel.

All around the hotel are New England prints.

The hotel provides a local newspaper each day.

Let’s explore the area

Before I checked in, I decided to explore Woodstock and the surrounding area. It was a fun-filled day! Here are some things I did:

First, I went to the Vermont Institute of Natural Science and fell in love with all the rescue birds. I also did their forest canopy walk, watched a live bird program, and walked their nature trails.

No trip to Woodstock is complete without heading to Sugarbush Farm where I walked the maple trail, visited with adorable cows, and tasted their homemade cheddar cheese.

I tasted delicious jam at Blake Hill Preserve. If you go, make sure you try their yummy ice cream they make with their own jam.

I sampled some lovely spirits at Silo Distillery. (Bring home their lavender cosmo)

I walked through the Quechee Covered Bridge

and shopped at Simon Pierce.

Time for dinner!

There are lots of dining options within walking distance from the hotel. I met a college friend at Dr. Coburns Tonic. I strongly recommend the Coburn Burger. It had a nice kick to it!

Let’s walk down to the river.

Let’s do a fire

After dinner I walked over to the fire pit by the river. It was so beautiful enjoying a glass of wine while watching the sun set and listen to the river flowing by.

After an amazing night’s sleep, I decided to start my day with a cup of coffee and the paper.

Since it was a beautiful day, I walked in to town and grab some breakfast. The walk from the hotel, with its tree-lined streets are so lovely.

I enjoyed a lavender latte and spinach pastry at Dreamscape Coffee.

I spent the morning poking in to all the boutique stores in town before heading home.

Who would I recommend it to?

I’d recommend The Shire to couples looking for a romantic getaway,

solo travelers needing a chill retreat,

or anyone planning a New England road trip.

Families would be comfortable here too, especially with the larger rooms and river access for kids to play. And if you’re into outdoor adventures—hiking, biking, skiing—it’s a great home base.

What can you do in the area?

Explore Downtown Woodstock – shops, galleries, and local cafes galore

Hike Mt. Tom – accessible trails with amazing views

Visit Billings Farm & Museum – great for families or history buffs

Go skiing or snowboarding – close to Killington and Suicide Six

Covered Bridges Tour – don’t miss the Middle Covered Bridge right in town

Restaurants in the area:

Worthy Kitchen: A vibrant farm‑to‑table diner loved for its comfort‑food classics—think gooey Vermont cheddar mac ‘n’ cheese, juicy burgers, plus poke and rice bowls with a twist. Don’t miss their craft beer lineup and signature Worthy Donuts

Santé: Woodstock’s upscale bistro spotlighting seasonal, locally sourced ingredients in small plates and handcrafted cocktails—from fresh meats and fish to veggie-forward dishes, all wrapped in a cozy, elegant atmosphere .

Au Comptoir: A sleek, cocktail‑centric bar accentuated with marble and wood décor, offering an inventive drink menu paired with light bites—perfect for an evening sip-and-snack .

  Ransom Tavern (at Kedron Valley Inn) Out in South Woodstock, this Italian‑inspired tavern serves wood-fired pizzas, farm-fresh cheese platters, and craft cocktails in a rustic, scenic setting

Village Butcher: A beloved deli‑bakery hybrid offering custom-cut meats, sandwiches, salads, and a curated wine & cheese selection—ideal for a casual lunch by the river.

Cloudland Farm: An authentic farm-to-table dining experience set on a working family farm; enjoy a seasonal, chef-curated three‑course prix‑fixe meal surrounded by hillside views.

The Prince & The Pauper: A refined downtown standout serving elegant Vermont classics, creative cocktails, and a prix-fixe menu in a historic, romantic atmosphere—always a top pick .

The Mill at Simon Pearce (Quechee – short drive away): Perched over a river and covered bridge, this romantic riverside restaurant features locally sourced dishes served on handmade glassware—plus you can watch live glassblowing

Tips for Planning your Stay

Parking: There is ample complimentary on-site parking.

Check-in: 3:00 Check-out: 11:00

Room choice? I would get a room with a river view.

They are currently offering house cleaning services.

The Shire

46 Pleasant St

 Woodstock, VT 05091

833-549-2370

CLICK HERE TO GET TO THEIR WEBSITE

Give them a follow

Instagram

Facebook

A warm thank you to The Shire for having me as your guest. Whether you’re coming for fall foliage, a winter wonderland escape, or just some peaceful R&R, The Shire makes it easy to soak up all the charm that Woodstock has to offer. As always, all experiences and opinions are 100% of MyTravelingKids.com.