The Perfect 3-Day Romantic Fall Getaway in Woodstock, Vermont

If you're dreaming of crisp air, vibrant foliage, cozy walks, and incredible food, Woodstock might just be the perfect spot for you. Here’s a 3-day itinerary that combines art, outdoor adventures, and delicious farm-to-table dining.

Day 1: Arrival and Exploring the Local Art Scene

Once you arrive in Woodstock, it’s like stepping into a postcard. The streets are lined with quaint shops and historic buildings, with pops of fall colors everywhere. After settling in, I recommend starting your day with a hearty breakfast at Mon Vert Café. You’ll love their local, organic ingredients and laid-back vibe.

After breakfast, take some time to wander through town and explore Woodstock’s art scene. Gallery on the Green is a must-see for art lovers, with work from local artists, and Farmhouse Pottery lets you watch artisans craft their beautiful pottery. It’s also a great spot to pick up a handmade souvenir to remember your trip.

In the afternoon, visit Billings Farm & Museum to experience Vermont’s farming history. It's the perfect blend of outdoor fun and local culture, and you might even catch a cheese-making demo. Finish your first day with dinner at Simon Pearce in nearby Quechee. Before you sit down to eat, watch the glassblowers in the workshop, then enjoy your meal overlooking the river. Trust me, the setting and food are magical.

Day 2: Hiking, Apple Picking, and Tasting Vermont’s Best

After a quiet night’s sleep, start day two with breakfast at Mountain Creamery—their pancakes are incredible! Then, lace up your hiking boots and head to Mount Tom. The Faulkner Trail is a moderate hike that takes you to the summit for breathtaking views of Woodstock and the surrounding fall foliage. It’s the perfect way to take in the crisp autumn air and spend some uninterrupted time together.

After your hike, stop for lunch at Woodstock Inn’s Red Rooster for a farm-to-table meal that will hit the spot after a morning of exploring. Then, make your way to Pomfret Hills Orchard for some classic fall fun—apple picking! There’s nothing like wandering through the orchard, grabbing fresh apples, and soaking in the mountain views.

While you’re out, take a quick detour to Sugarbush Cheese & Maple Farm. They offer free cheese tastings (yes, please!) and delicious maple syrup. Pick up some goodies to take home—or snack on during the rest of your trip.

For dinner, I recommend The Prince & The Pauper in Woodstock. The ambiance is cozy and romantic, with a menu that showcases local ingredients and creative takes on New England classics. It’s the perfect spot for a special evening.

Day 3: Scenic Drives, Covered Bridges, and Relaxation

On your last day, take things slow and enjoy a leisurely breakfast before heading out to Quechee Gorge. Known as Vermont’s "Little Grand Canyon," it’s especially beautiful in the fall. A short hike along the gorge offers gorgeous views, and it’s the perfect spot to snap a few photos.

Afterward, enjoy a drive around the area, making sure to stop at Woodstock’s famous covered bridges, like the Middle Covered Bridge and Taftsville Covered Bridge. These historic structures are surrounded by incredible fall colors and are ideal for a romantic stroll or photo opp.

Wrap up your day with a relaxing afternoon at the Woodstock Inn Spa. Whether you opt for a massage or just take in the peaceful surroundings by their heated pool, it’s the perfect way to unwind before heading back to reality.

Final Thoughts

There’s something so special about Woodstock in the fall. From the beautiful hikes and scenic drives to the quiet moments spent wandering through town, it’s the perfect place to recharge and reconnect with your partner. If you’re dreaming of a romantic fall escape, I can’t recommend this Vermont getaway enough. The beauty of the season, the slow pace of life, and the delicious farm-to-table meals make for a weekend you’ll never forget.

Ready to plan your own getaway? Let me help you craft the perfect vacation, whether it’s a romantic weekend or a family adventure. From cozy B&Bs to the best local experiences, I’ll take care of the details so you can simply enjoy. Reach out, and let’s make your dream trip a reality!