Top Vermont Seasonal & Special Occasions

This tour is built just for you! You provide what you'd love to see and do (scenery, farms, photography, food, artisans, etc.) and what you'd rather skip and I'll create a customized itinerary for your day. We'll travel in a built-for-back roads Bronco, with a (weather permitting) top-down, open air experience you won't soon forget! As much as possible, we keep off the main routes and stick to dirt roads where traffic doesn't exist, the scenery is breathtaking, and hidden views abound. There will be plenty of opportunities to pause and take it all in. Be sure to check out the Vermont Wayfinders website for more information on tours and availability, including add-on options like heading to the top of Killington or going for a horse-drawn carriage ride. The places provided listed here are just the start; this truly is a signature tour, tailored to you and your small group.

Elevate your special occasion with a private trolley transportation from us. Ideal for weddings, birthdays, and family gatherings, this classic trolley offers comfortable and flexible transportation tailored to your needs. Customize your experience by choosing your route, schedule, and level of narration while enjoying the journey with up to 32 guests. Bring your decorations, food, and drinks to match your celebration's theme. - Perfect for weddings, parties, and group celebrations - Fully customizable with various routes and durations - Comfortable seating for up to 32 guests - Enjoy a social atmosphere while traveling together

In recent years, Vermont has become known for its artisanal food scene, as well as its destination-worthy craft breweries and distilleries—and this small-group tour makes it easy to taste the best of the Green Mountain State. Following pickup at your Killington or Woodstock accommodation, travel via air-conditioned vehicle to three breweries, two distilleries, and additional foodie spots, and taste what interests you most (own expense).

No matter the occasion—whether it's an anniversary, birthday, corporate event, day out with friends, or a girls' getaway—you'll likely need a designated driver, and that's where we come in. With a maximum of six customers per tour, this experience is intimate and feels like traveling with a group of friends! We are a small boutique tour company with over decade of experience! Available in spring and summer only, this guided tour visits three Vermont wineries, one hard cidery, and other local attractions. Most wines in Vermont are crafted from hybrid grape varieties suited to the harsh climate. When booking a hotel for this tour, please choose a location in either the Burlington, South Burlington or Killington areas. We offer door-to-door pick-up service! Available Wednesday – Sunday ONLY

See quaint villages, striking scenery, and more on this full-day, small-group tour of northern Vermont. Leave the driving and logistics to your guide, and set off via minivan—your first destination is the famed Ben & Jerry’s Factory in Waterbury, where you can enjoy tasty samples. Tour a cider mill before continuing to Smugglers’ Notch State Park, the von Trapp Family Lodge, the village of Stowe, and more.

It takes guests through Burlington, Shelburne, Monkton, Heinsberg and the Lake Champlain corridor during peak foliage season. The tour uses a classic red-and-green trolley (a bus styled as a trolley) and offers a journey focused on Vermont’s culture, landscape, and seasonal beauty. It goes through Chittenden County’s most vibrant fall corridors—lake views, rolling farmland, and tree‑lined backroads known for strong color change. It has 3stops that offer very unique relation as breaks while connecting and seeing and blending with the local things.

There’s nothing like fall in Vermont! The crisp air, the burst of color from maple leaves, and sunlight filtering through the trees make every back road feel like an adventure. Be sure to check out the Vermont Wayfinders website for more information on tours and availability, including add-on options like heading to the top of Killington or going for a horse-drawn carriage ride. Your curated tour takes you through the most scenic routes during foliage season. Whether you’re looking for panoramic views, covered bridges framed by colorful leaves, or charming villages bursting with fall vibes, we put together each itinerary to give you the ultimate Vermont fall experience. Tour Highlights: - Breathtaking foliage views from iconic overlooks and winding back roads - Visits to cozy Vermont towns - Stops at local farms, breweries and hidden vistas - Chances to wander near fields and forests and capture postcard-worthy photos