Vermont’s beauty lies in its diverse natural surroundings, pristine lakes, vibrant state and local parks, historic downtowns, and winding roads that pass through our small villages and towns. A four-season destination, the Rutland Region offers unparalleled recreation and other activities for your enjoyment.
Four seasons in the Rutland Region
Rutland County is a 27-town region where mountain peaks, lakes, historic downtowns and working farms sit close together. Use this guide to plan by season, by weather or by town, and follow the links to the full activity lists.
Winter: ski, ride and skate
Killington. Killington Resort is the largest ski area in the eastern United States, with seven mountain areas, 155 trails and six terrain parks. Killington Peak, at 4,241 feet, is the second-highest peak in Vermont. Pico Mountain, in Mendon, is also a downhill option.
In and around Rutland. Pine Hill Park offers 17 miles of single-track trail across 325 acres, and in winter it is used for snowshoeing, backcountry Nordic skiing and fat-tire biking. Pittsford’s trail network supports walking, snowshoeing and cross-country skiing through open fields and woodland. Indoor ice rinks keep skating going all winter.
On the ice. When Chittenden Reservoir freezes over it becomes a popular spot for ice fishing. Snowmobiling is also part of the region’s winter mix.
Summer: lakes, trails and festivals
On the water. Lake Bomoseen is the largest lake located fully within Vermont, with boating and kayaking. Lake St. Catherine in Poultney covers 852 acres and offers boating, fishing, swimming and camping. Chittenden Reservoir covers 721 acres and has rentals for canoes, kayaks and stand-up paddleboards. Halfmoon Pond State Park in Hubbardton has 52 tent and RV sites, five cabins and 11 lean-tos, with kayaks, canoes and paddleboats to rent.
On the mountain. Killington’s warmer months bring mountain biking and golf, plus an adventure center with the Beast Mountain Coaster, the Soaring Eagle and Alpine Tubing. Moosalamoo National Recreation Area, inside the 400,000-acre Green Mountain National Forest, is known for hiking and biking, and Poultney’s Slate Valley Trails have made the town a mountain biker’s destination.
Markets, concerts and history. Rutland’s farmers’ market runs outdoors in Depot Park from May through October. Fair Haven’s town park hosts band concerts through the summer, from early June to mid-August. In the third week of July, Hubbardton Day at the Battlefield includes a barbecue, games, a concert and fireworks. Pond Hill Ranch in Castleton runs a pro rodeo in the summer months and offers trail rides.
Fall: foliage, covered bridges and festivals
Foliage and views. The Taconic Mountains around Danby and Mount Tabor are known for fall color. The 1.9-mile Deer Leap Overlook trail in Killington is suitable for hikers of all abilities and offers views of the Green Mountain valley. The Japanese Zen Garden at Taconic Mountains Ramble State Park in Hubbardton is open from Memorial Day through early October.
Scenic drives. The Crossroad of Vermont Byway follows Route 4 across the Green Mountains, with stops in Killington and West Rutland. Slower dirt roads lead to historic covered bridges, including four in Pittsford: Hammond, Cooley, Gorham and Depot.
Whoopie Pie Festival. Each September downtown Rutland hosts the Whoopie Pie Festival. The fifth annual festival, on September 12, 2026, drew more than 8,000 attendees and 13 whoopie pie vendors.
Any season, any weather
Museums and landmarks. The Vermont Marble Museum in Proctor displays a white marble bust of every U.S. president. Nearby, Wilson Castle sits on a 115-acre estate with three floors and 32 rooms. Wonderfeet Kids’ Museum in Rutland is a good family stop. The Vermont Danby Quarry, the largest underground marble quarry in the world, is not open to visitors but offers a virtual tour. Hubbardton Battlefield marks the only Revolutionary War battle fought entirely on what is now Vermont soil.
Arts and culture. Catch a show at the historic Paramount Theatre or at Casella Theater on the Castleton campus, take a class at the Chaffee Art Center, walk Rutland’s murals and sculpture trail, or browse the Brandon Artists Guild. West Rutland’s Carving Studio and Sculpture Center has taught sculpture for more than 30 years.
Rainy-day options. The region has an indoor rock climbing center, indoor ice rinks and an indoor golf center. In winter Rutland’s year-round farmers’ market moves indoors to the Vermont Farmers Food Center.
Explore by town
Rutland City and Rutland Town
Rutland is Vermont’s third-largest city, with a walkable downtown of shops, restaurants, galleries, murals and a sculpture trail, about 20 minutes from Killington. Plan a show at the historic Paramount Theatre, a visit to Wonderfeet Kids’ Museum, or a walk through Center Street Marketplace. Gill’s Delicatessen has been a local staple for more than 50 years, and The Sandwich Shoppe is a multi-generational family business. Pine Hill Park is minutes from downtown.
Killington
Killington is a small mountain community built around the resort. Beyond skiing, riding and mountain biking, it has hiking at Thundering Brook Falls and Deer Leap Overlook, and fishing, kayaking and canoeing at Kent Pond and Colton Pond. Most restaurants and shops, including ski and bike gear, are on Killington Road, the access road to the resort.
Castleton
Castleton sits seven miles from the New York border and is home to Vermont’s oldest institution of higher learning. The 165-acre campus borders the Delaware and Hudson Rail-Trail, which connects Castleton and Poultney and is good for walking, running and picnics. Eat at the Birdseye Diner, housed in a 1940s Silk City dining car, and head to nearby Lake Bomoseen for year-round recreation. The campus hosts the annual Shrine Maple Sugar Bowl, summer concerts and performances in Casella Theater.
Proctor
Proctor lies along the Otter Creek valley and grew up around the Vermont Marble Co. The Main Street bridge is built of white Vermont marble quarried nearby, and the Vermont Marble Museum occupies a wing of one of the former company buildings. Wilson Castle, a mid-19th-century mansion on 115 acres, offers tours; check availability before you go.
Brandon
Brandon, between Rutland and Middlebury, calls itself the “art and soul” of Vermont. Its walkable downtown has galleries, studios, shops and restaurants, including the Brandon Artists Guild with work by Warren Kimble and more than 50 other artists, plus the Vermont Folk Art Gallery and Compass Music and Arts Center. Moosalamoo National Recreation Area is close by, and Branbury State Park on Lake Dunmore has a sandy beach, picnic areas and campsites.
Pittsford
Known as the Sunshine Village, Pittsford is a good base for a covered-bridge driving tour and for trail walking, bird watching and snowshoeing. It also has an 18-hole disc golf course next to its recreation trails. Stop at Kamuda’s Country Market, a third-generation family store open since December 1939, or the New England Maple Museum.
Poultney
Poultney, in the slate valley, has a small downtown with a bookstore, The Original Vermont Store, a florist and an antiques shop, plus places to eat such as Taco Experiment, Perry’s Main Street Eatery and Taps Tavern. Outside town, find the historic East Poultney Green, Whaleback Vineyard and the East Poultney General Store. Lake St. Catherine and the volunteer-built Slate Valley Trails cover water and wheels.
Fair Haven
Fair Haven is widely regarded as the slate capital of the United States. Its historic Village Green, listed on the National Register of Historic Places, is surrounded by Victorian architecture, including the Marble Mansion Inn, and hosts concerts in the warmer months. Shop at Carl Durfee’s Store and have breakfast at the Wooden Soldier.
Hubbardton and Sudbury
Hubbardton is best described as historic. The Battle of Hubbardton took place here in 1777, and the Battlefield keeps its wide-open meadows and mountain views. Taconic Mountains Ramble State Park, on 204 acres, is open from late June through Labor Day, and Halfmoon Pond State Park offers camping, cabins, fishing and boat rentals.
Danby and Mount Tabor
The southernmost towns of the county sit in the Taconic Mountains, between Rutland and Manchester. The Vermont Danby Quarry has produced Imperial Danby Marble since the early 1900s, and that marble has been used in notable buildings including the Supreme Court building and the Jefferson Memorial in Washington, D.C. Hikers can take the Little Rock Pond Trail, a section of the Appalachian/Long Trail.
Wallingford and Tinmouth
Wallingford’s Main Street was added to the National Register of Historic Places in the early 1980s. Handmade in Vermont, in a stone building on Main Street, is operated by a consortium of Vermont artists, and The Sparkle Barn sells handcrafted art and gifts. Sal’s, the Main Street Café and the Victorian Inn are good places to eat.
West Rutland
West Rutland blends nature and art. The Marsh Boardwalk is a designated Important Bird Area where visitors may see species such as the Virginia Rail, Sora, American Bittern and Marsh Wren, and Grandpa’s Knob offers higher-elevation views. The Carving Studio and Sculpture Center carries on the town’s marble heritage.
Chittenden and Mendon
Chittenden has one small country store and no stoplights. Chittenden Reservoir, at 721 acres, is open for fishing, swimming and boating with motors up to 15 horsepower, and nearby Lefferts Pond is home to moose, loons and black bears; both are day-use only. Mountain Top Inn & Resort is a four-season destination on 700 private acres. Mendon is home to Pico Mountain, Mendon Mini Golf & Snack Bar and Mendon Mountain Orchards.
Eat, shop and plan ahead
Dining ranges from country inns and breweries to diners and coffeehouses, and many restaurants source from local farms. See the full list on our dining page, browse outdoor and indoor activities and historic sites, and check the events calendar for what is happening this month. Thinking of moving here? Read our guide to moving to Rutland County. Questions? Call the Chamber & Economic Development of the Rutland Region at (802) 773-2747.
The Chamber & Economic Development of the Rutland Region is seeking to keep our activities board up to date. Not seeing an activity, business, or location that should be listed? Reach out to our Communications & Marketing Manager, Matt Britt at [email protected].