Things to Do in Southern Vermont – Your Complete Travel Guide

Exploring things to do in Southern Vermont is an experience filled with charming small towns, forest-lined roads, beautiful mountain views, and peaceful lakesides that feel like a postcard come to life. Southern Vermont has a reputation for quiet luxury, farm-to-table food, covered bridges, nature escapes, and small communities that welcome travelers warmly. Whether you’re traveling solo, as a couple, with friends, or with family, the region offers something memorable for everyone. From scenic drives and outdoor adventures to skiing, shopping, history, and wine-tasting, the opportunities to relax or explore are endless.

What makes Southern Vermont extra special is its slow, calming pace. It’s one of those rare destinations where you can spend the morning hiking, the afternoon roaming art galleries, and the night enjoying a cozy fireside dinner at a local inn. This blog covers the best things to do in Southern Vermont, including hidden gems, must-visit towns, top attractions, outdoor adventures, and food experiences that define Vermont’s welcoming countryside charm.

1. Explore the Historic Charm of Manchester

When it comes to things to do in Southern Vermont, Manchester is always at the top of the list. This beautifully preserved village sits at the base of Mount Equinox and is known for its elegant white-marble buildings, boutique shops, antique stores, and stunning mountain views. Travelers love the blend of luxury and rustic charm—think fine dining paired with small-town friendliness. Manchester offers experiences for every type of traveler, from history lovers to outdoor enthusiasts and retail therapy seekers.

One of the highlights is Hildene, the historic Lincoln family mansion featuring gardens, walking trails, and a goat farm. Downtown Manchester is ideal for strolling, with outlets, cafés, bookstores, and galleries lined along walkable streets. If you’re visiting during fall foliage, the region transforms into a carpet of reds and golds, making it one of the most photogenic destinations in New England.

2. Visit the Bennington Battle Monument

A list of things to do in Southern Vermont would be incomplete without mentioning the iconic Bennington Battle Monument. Standing 306 feet tall, this stone obelisk commemorates a major Revolutionary War victory and is Vermont’s tallest man-made structure. Taking the elevator to the top offers breathtaking views of the mountains, valleys, and towns across three states—Vermont, Massachusetts, and New York. It’s a must-visit for history lovers and first-time travelers to the region.

Around the monument, you’ll find charming neighborhood streets, small museums, and lush green surroundings perfect for photography. The nearby Bennington Museum houses exhibits on local art and culture, including the world’s largest collection of Grandma Moses paintings. Together, the monument and museum create a fascinating journey through Vermont’s history, making them essential stops for anyone exploring Southern Vermont.

3. Hike and Drive Through the Green Mountains

Outdoor lovers searching for things to do in Southern Vermont will find endless adventures in the Green Mountain National Forest. The forest spans miles of pristine wilderness offering scenic trails, waterfalls, overlooks, and wildlife sightings. Whether you enjoy an easy walk or a full-day hike, the region has trails for all skill levels. Popular choices include Lye Brook Falls Trail, Stratton Mountain Trail, and the picturesque Equinox Pond loop. Each trail rewards hikers with beautiful views and peaceful forest surroundings.

In addition to hiking, the forest provides excellent opportunities for scenic drives. The Molly Stark Byway is especially famous, stretching from Brattleboro to Bennington with panoramic views and roadside stops worth exploring. Visiting during fall makes the experience even more magical as the countryside bursts into vibrant colors, offering some of the best leaf-peeping in New England.

4. Enjoy Skiing and Winter Sports at Mount Snow

For winter travelers seeking things to do in Southern Vermont, Mount Snow is one of the region’s top attractions. Known for its excellent terrain, professional snowmaking system, and family-friendly atmosphere, it attracts skiers and snowboarders from across the Northeast. The mountain offers trails for beginners, intermediates, and advanced riders, making it ideal for all levels. Gondolas, ski schools, and equipment rentals make the experience smooth and accessible for new visitors.

But Mount Snow isn’t just a winter destination. In the warmer months, it transforms into a hub for mountain biking, scenic chairlift rides, hiking, and festivals. Fall brings vibrant foliage views from the summit, while summer weekends feature concerts, craft fairs, and outdoor events. No matter the season, Mount Snow provides adventure, relaxation, and plenty of scenic beauty.

5. Discover the Covered Bridges of Southern Vermont

Covered bridges are a classic part of the Vermont landscape, and exploring them is one of the most relaxing things to do in Southern Vermont. These wooden structures are both beautiful and historically significant, adding rustic charm to the region’s towns and countryside. Some of the most famous include Henry Bridge, Silk Bridge, Paper Mill Bridge, and the iconic Arlington Green Covered Bridge. Each bridge tells a story and offers perfect opportunities for photography, quiet walks, and connecting with Vermont’s heritage.

Many covered bridges are located near rivers, forests, and picnic areas, making them great spots for a peaceful afternoon. Some even have small walking trails nearby that let you enjoy the surrounding scenery. Whether you’re a photography lover or someone who appreciates scenic architecture, touring these bridges is a memorable way to explore Southern Vermont’s rural beauty.

6. Wander Through Brattleboro’s Artsy Downtown

Brattleboro is one of the most vibrant towns to visit if you’re searching for cultural things to do in Southern Vermont. Known for its artistic spirit, colorful murals, craft shops, and independent bookstores, the town is full of character. Visitors love browsing handmade goods, visiting local studios, and enjoying live music performances. The Brattleboro Food Co-op is a local favorite offering organic foods, Vermont products, and delicious café items perfect for a quick meal.

Art galleries line the downtown streets, and the Brattleboro Museum & Art Center showcases rotating exhibits from regional and international artists. The town also hosts festivals throughout the year, including the famous Strolling of the Heifers parade. With its riverfront views, lively culture, and friendly vibe, Brattleboro provides a refreshing mix of creativity and small-town charm.

7. Relax at Local Wineries and Breweries

Sampling local flavors is one of the most enjoyable things to do in Southern Vermont, especially for wine and craft beer lovers. The region is home to award-winning vineyards and breweries offering tastings, tours, and scenic outdoor seating. Top spots include Honora Winery, Putney Mountain Winery, and the popular Whetstone Beer Co. in Brattleboro. Each destination provides a unique atmosphere perfect for an afternoon getaway.

Many wineries offer beautiful views of rolling hills and farm landscapes, making them ideal for romantic dates or relaxing group outings. You can enjoy fruit wines, cider tastings, fresh brews, and seasonal specialties made using local ingredients. Some locations even host weekend events, live music, and food pairings to enhance the experience.

8. Visit Farm Markets and Maple Syrup Farms

Exploring Vermont’s agricultural side is a wonderful addition to your list of things to do in Southern Vermont. The region has many family-owned farms where visitors can enjoy fresh produce, farm tours, and maple syrup tastings. Maple syrup is a Vermont signature, and visiting sugarhouses during sugaring season (late winter to early spring) is a fun and educational experience. You can see how sap is collected, boiled, and turned into rich golden syrup.

Farmers’ markets in towns like Manchester, Bennington, and Brattleboro are perfect for buying local cheeses, baked goods, vegetables, and homemade jams. Many markets also feature live music, artisan crafts, and food stalls. It’s one of the best ways to connect with Vermont’s farm-to-table culture while supporting local growers and creators.

9. Explore Grafton – A Perfect New England Village

Grafton is often described as one of the prettiest small towns in New England, making it a top recommendation for travelers searching for peaceful things to do in Southern Vermont. The town feels untouched by time, with restored buildings, quiet streets, local museums, and boutique inns. It’s the kind of place where you can walk slowly, breathe fresh air, and admire Vermont’s rural charm.

The Grafton Village Cheese Company is a popular stop where visitors can sample locally crafted cheeses and watch the cheese-making process. The town also offers scenic hiking trails, art galleries, and the Grafton Historical Society. For travelers wanting a quiet, authentic Vermont experience, Grafton is a timeless treasure.

10. End Your Trip With a Scenic Lake Day

Enjoying the region’s lakes is one of the most relaxing things to do in Southern Vermont, especially during summer and early fall. Lake Whitingham (also known as Harriman Reservoir) offers kayaking, swimming, boating, and peaceful picnicking areas. Its calm waters and mountain backdrop make it perfect for both adventure and relaxation.

Smaller lakes and ponds across the region offer fishing, paddleboarding, and sunrise photography opportunities. Many travelers enjoy ending their Southern Vermont trip with a lakeside day to unwind and reflect on the region’s natural beauty.

Final Thoughts on Things to Do in Southern Vermont

Whether you’re planning a long vacation or a weekend getaway, exploring the things to do in Southern Vermont will leave you with unforgettable memories. The region’s combination of outdoor recreation, charming towns, scenic views, farm experiences, and rich history makes it a destination you’ll want to return to again and again. Southern Vermont’s peaceful atmosphere offers the perfect escape from busy city life—inviting you to slow down, breathe deeply, and enjoy the simplicity and beauty of nature and community.