🍁 SOUTHERN VERMONT ROAD TRIP | Quechee Gorge, Woodstock, Manchester, Bennington & Brattleboro

Come along with MiWayJourneys as we explore some of the most beautiful towns, scenic drives, historic landmarks, local restaurants, breweries, shops, and hidden gems on an unforgettable Southern Vermont road trip. Our Vermont adventure takes us from the dramatic cliffs of Quechee Gorge and classic New England streets of Woodstock south through Manchester and Bennington, across the mountains to Wilmington, and finally into the creative river town of Brattleboro. If you're planning a Vermont road trip, searching for the best places to visit in Vermont, or just looking for ideas for your next New England getaway, this journey is packed with places worth adding to your itinerary. 🏞️ QUECHEE GORGE | Vermont's Little Grand Canyon We begin at Quechee Gorge, one of Vermont's best-known natural attractions. Carved by the Ottauquechee River, the gorge offers dramatic views from above and hiking opportunities along the river. 📍 Places to explore: • Quechee Gorge • Quechee State Park • Ottauquechee River • Quechee Village • Simon Pearce Mill • Vermont Institute of Natural Science (VINS) 🍽️ Look for local cafés, Vermont cheeses, maple products, farm-to-table meals and craft beverages around Quechee and nearby Woodstock. 🏘️ WOODSTOCK | Classic New England Vermont Next we're exploring Woodstock, Vermont, a quintessential New England village filled with historic architecture, covered bridges, shops and beautiful mountain scenery. 📍 Places to explore: • Woodstock Village • Middle Covered Bridge • Billings Park • Billings Farm & Museum • Marsh-Billings-Rockefeller National Historical Park • Taftsville Covered Bridge 🍴 Woodstock is a great stop for Vermont comfort food, locally sourced meals, bakeries, cafés and a relaxing drink before continuing south. ⛰️ MANCHESTER | Mountains, History & Vermont Shopping Surrounded by the Green Mountains, Manchester, Vermont combines outdoor adventure, historic New England charm, great food and some of the state's best-known shopping. 📍 Places to explore: • Hildene, The Lincoln Family Home • Equinox Preserve • Mount Equinox • Manchester Village • Northshire Bookstore • Manchester Designer Outlets 🍺 Make time for the Manchester area's restaurants, cafés, taverns and Vermont craft beer scene. It's also a great place to sample locally produced cheeses, maple products and specialty foods. 🏛️ BENNINGTON | Revolutionary Vermont Our journey continues into Bennington, where Vermont history takes center stage. 📍 Places to explore: • Bennington Battle Monument • Old First Church • Bennington Museum • Robert Frost's grave • Downtown Bennington • Historic covered bridges Bennington's downtown makes an excellent stop for lunch, coffee or a locally brewed beer before heading deeper into Southern Vermont. 🌲 WILMINGTON | Scenic Green Mountain Escape Set along the Molly Stark Byway, Wilmington is a classic Southern Vermont mountain town and an ideal base for exploring the Deerfield Valley. 📍 Places to explore: • Historic Downtown Wilmington • Lake Whitingham • Molly Stark Scenic Byway • Harriman Reservoir • Mount Snow area • Southern Vermont hiking trails 🍻 Wilmington offers a fun collection of independent restaurants, taverns, cafés and craft beverage stops—perfect after a day exploring the mountains. 🌉 BRATTLEBORO | Arts, Food & the Connecticut River We finish our Southern Vermont road trip in Brattleboro, a lively town along the Connecticut River known for its arts community, independent businesses, local food and Vermont character. 📍 Places to explore: • Downtown Brattleboro • Brattleboro Museum & Art Center • Retreat Farm • Creamery Covered Bridge • Connecticut River • Local galleries and independent shops 🍽️ Brattleboro is one of my favorite kinds of travel stops: a walkable downtown where you can explore local restaurants, cafés, bakeries and craft beverages while discovering a little of the town's personality. 🚐 MiWayJourneys Travel Tips 🍁 Fall: Late September through mid-October can bring spectacular foliage, but expect larger crowds and higher lodging prices. 🚗 A must-watch for road trip enthusiasts seeking scenic drives and unique adventures 🧳 Packed with actionable how-to travel tips for first-time visitors 💡 Don’t Forget! Like, comment, and subscribe to MiWayJourneys for more incredible travel vlogs, destination guides, and adventure stories every week! Helpful Links & Resources: 🎥 Check out the planning video:    / @miwayjourneys_travel   📸 Follow us for behind-the-scenes updates:   / miwayjourneys   Support my efforts by buying me a cup of coffee: https://buymeacoffee.com/miwayjourneys