Discovering Woodstock, Vermont: A Solo Female Traveler’s Journey

Woodstock, Vermont, is a charming New England village that offers an unforgettable experience for solo travelers. Whether you’re here for a weekend getaway or an extended stay, this guide will walk you through the best places to eat, activities to do, and the most comfortable accommodations, all from the perspective of a solo female traveler.

woodstock restaurants

Where to Eat in Woodstock, Vermont: The best restaurants

When I first arrived in Woodstock, my senses were immediately awakened by the aromas wafting from the local eateries. As someone who loves to explore a destination through its food, I made it my mission to sample the best this quaint town has to offer.

Breakfast Bliss at Mon Vert Cafe
My mornings in Woodstock began at Mon Vert Cafe, a local favorite for breakfast and lunch. The line can get long, so it’s best to arrive early. The cafe has a cozy, welcoming atmosphere, reminiscent of a charming small-town eatery with a dash of upstate New York flair. I indulged in their breakfast burrito, a hearty dish packed with fresh, local ingredients, and their challah French toast, which was perfectly sweet and fluffy. The baked goods here are made fresh daily, making it the perfect spot to fuel up for a day of exploration.

Comfort Food with a Twist at Worthy Kitchen
For lunch or dinner, Worthy Kitchen became my go-to spot. This modern pub offers classic comfort food with a fresh, contemporary twist. Their menu is a delightful mix of familiar dishes and unexpected flavors. I couldn’t resist their Vermont cheddar mac and cheese, a gooey, comforting dish that felt like a warm hug on a plate. If you’re in the mood for something lighter, their poke and rice bowls are just as satisfying. The black bean veggie burger is a must-try for vegetarians. Pair your meal with one of their craft IPAs for the full experience.

Dining with a View at Simon Pearce Restaurant
One of my most memorable meals in Woodstock was at Simon Pearce Restaurant. Perched above the Ottauquechee River, this restaurant offers stunning views that complement its creative seasonal menu. I dined on their terrace, savoring dishes like zucchini and squash fritters with tomato chutney, Vermont cheddar cheese soup, and salmon served over a polenta cake with a mustard maple marinade. Each bite was a testament to the region’s rich culinary traditions, all while enjoying the serene river views and the warm ambiance of the restaurant.

Cozy Evenings at Richardson’s Tavern
For a cozy, quintessential Vermont dining experience, Richardson’s Tavern is the place to be. The atmosphere here is like stepping into a lodge, with its warm fireplace and comfortable booth seating. The service may be a bit leisurely, but it’s worth the wait, especially for their Vermont Maple cake dessert. This tavern is the perfect spot to wind down after a day of exploring Woodstock.

Other Notable Mentions
Although I didn’t have time to visit, The Prince and The Pauper and Cloudland Farms are high on my list for my next visit. The former is known for its elegant take on Vermont classics, while the latter offers a unique farm-to-table dining experience where the menu is chef’s choice for the day.

Read more: Montauk NY: Things to do, places to stay and top attractions

Things to do: Activities to Enjoy in Woodstock, Vermont

Woodstock isn’t just about great food—it’s also a haven for outdoor enthusiasts and those looking to soak up some local culture. As a solo traveler, I found plenty of activities to keep me busy, from hiking scenic trails to exploring local art galleries.

Exploring the Marsh-Billings-Rockefeller National Historical Park
No trip to Woodstock would be complete without a visit to the Marsh-Billings-Rockefeller National Historical Park. This park offers a perfect blend of natural beauty and historical significance. I spent a tranquil afternoon hiking through its well-maintained trails, surrounded by vibrant fall foliage. The park’s landscape is a living testament to the conservation efforts of its namesake families, and the guided tours provide fascinating insights into their legacy.

Strolling Through the Woodstock Village
Woodstock’s village is straight out of a postcard, with its historic buildings, charming boutiques, and friendly locals. I loved spending time just wandering the streets, popping into the various shops, and chatting with the shopkeepers. The Woodstock Farmers’ Market was a particular highlight, offering a bounty of local produce, artisanal goods, and homemade treats. It’s the perfect place to pick up some unique souvenirs or enjoy a fresh snack.

Visiting the Billings Farm & Museum
For a deeper understanding of Vermont’s agricultural heritage, the Billings Farm & Museum is a must-visit. This working farm and museum offer a glimpse into the state’s rural past. I enjoyed touring the farm, meeting the animals, and learning about traditional farming techniques. The museum’s exhibits are well-curated and informative, making it a great place for solo travelers interested in history and culture.

Taking in the Art at Collective, the Art of Craft
As an art lover, I was thrilled to discover Collective, the Art of Craft. This gallery showcases the work of local artists and artisans, offering everything from pottery and jewelry to textiles and paintings. The quality and creativity of the pieces on display are impressive, and I couldn’t resist purchasing a few items as mementos of my trip. The gallery staff were friendly and knowledgeable, making my visit even more enjoyable.

Relaxing at the Taftsville Covered Bridge
For a moment of peace and reflection, I visited the Taftsville Covered Bridge. This historic bridge is one of the oldest in Vermont, and it’s a beautiful spot for photography or just taking in the scenery. The sound of the river flowing beneath the bridge was incredibly soothing, and I found it to be a perfect place to unwind after a day of exploring.

Where to Stay in Woodstock, Vermont: The best hotels

Finding the right place to stay is crucial for any trip, and Woodstock offers a variety of accommodations that cater to different tastes and budgets. As a solo female traveler, safety, comfort, and convenience were my top priorities, and Woodstock did not disappoint.

woodstock things to do

Luxurious Stay at the Woodstock Inn & Resort
The Woodstock Inn & Resort is the epitome of New England luxury. From the moment I arrived, I was treated like royalty. The elegant décor, warm fireplaces, and lush gardens made it feel like a home away from home. The Inn offers a range of activities, from spa treatments to guided hikes, ensuring there’s always something to do. I stayed in a room with a four-poster bed and a view of the courtyard—every detail was perfect. The Inn’s central location made it easy to explore the rest of Woodstock, and after a long day, it was the perfect retreat to relax and recharge.

Charming Stay at The Shire Woodstock
For a more budget-friendly option without sacrificing comfort, The Shire Woodstock was a fantastic choice. The rooms are cozy, with rustic décor that adds to the Vermont charm. I loved waking up to views of the river and starting my day with a cup of coffee on the balcony. The Shire’s location is just a short walk from the village, making it convenient for solo travelers like me who prefer to explore on foot. The staff were incredibly welcoming and provided great recommendations for things to do in the area.

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Secluded Retreat at Twin Farms
If you’re looking for a truly unique and luxurious experience, Twin Farms is the place to be. Although I didn’t stay here during this trip, it’s on my bucket list for a future visit. This all-inclusive resort is nestled in the Vermont countryside, offering a secluded and peaceful retreat. The accommodations are stunning, with each cottage and suite featuring its own distinctive style. Twin Farms is perfect for those who want to disconnect and immerse themselves in nature, with activities like hiking, fly fishing, and even wine tastings available on-site.

Cozy B&B Experience at The Jackson House Inn
For a more intimate and personalized stay, The Jackson House Inn is a charming bed and breakfast that offers a cozy and welcoming atmosphere. The rooms are beautifully decorated, and the innkeepers go out of their way to make you feel at home. I particularly enjoyed the gourmet breakfast each morning, which featured local ingredients and was the perfect start to my day. The Jackson House Inn is located just outside the village, providing a peaceful setting while still being close to all the action.

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