We have been assembling this resource to help our guests and other visitors to the Brattleboro, Vermont area plan their trips. We hope that it is valuable to you.
Twice Upon a Time
This little gem of a consignment shop is located on Main Street in downtown Brattleboro. Its spacious and well stocked floors are filled with oddities and treasures of years gone by. There are more details of this shop and others downtown on our shopping page.
Route 5 Corridor
Leave our driveway and head North on Route 5. This drive is sprinkled with a selection of small antique shops and will take you through several other small Vermont towns.
Route 30 Corridor
A real antique lovers delight, route 30 north will take you past some real hidden gems. Pay attention as you pass through the seveal villages along the ride, there are many antique shops tucked away on side roads. There are some of our favorites on the shopping page.
The first friday of each month is gallery walk in Brattleboro. This Celebration of the Arts features over 40 different exhibits in galleries, cafes and other establishments. There are artists’ receptions, live music, a dance and other performances as well. There are several cultural institutions including the Brattleboro Music Center, Brattleboro Museum and Arts Center, and the Hooker Dunham Theater. In addition there are a number of restaurant and bar venues that offer live music and performing arts events.
Cross Country Skiing
The Brattleboro Outing Club
The Brattleboro Outing Club maintains 16 km of groomed trails at the Brattleboro Country Club. Fees are on the honor system. From our driveway, turn right and stay on Route 30 just past the Retreat. Turn left at Upper Dummerston Road. The club is about 1½ miles on your left. (Rental equipment is available on weekends).
In Grafton you will find groomed cross country trails at Grafton Ponds. Take Route 30 up to Townshend. Turn right onto Route 35 and head north to Grafton. Just before you reach town, you will see the cheese factory, covered bridge and ski center.
You can also find groomed trails at Mount Snow and at Stratton Mountain.
The summer guide still works!
Although many people consider hiking a summer sport, the same trails are often even more spectacular (and always less crowded) in the winter! Be careful of ice and slippery spots and of course, dress appropriately for the cold weather. Check out our hiking guide on our summer page.
The Retreat Meadows, located in our back yard, is frozen over each year and dotted with fishing shacks. There is often a cleared area right next to the road that makes for some wonderful skating. Remember that skating on open water can be extremely dangerous. Be careful of thin ice and always be aware of the conditions of the day!
Memorial Park (map directions to this location)
Memorial Park has a rink open to the public just on the other side of the covered bridge.
From our driveway head to the right (downtown) and make a right on route 9. Take route 9 to the covered bridge and make a left over the bridge. The park is right there.
On the local rivers (Connecticut and West) you can catch bass (small and large mouth), pike, pickerel, perch, walleye, yellow perch, white perch, shad, trout (in the spring, and whatever is still biting in the winter), bluegill and rock bass. On the Retreat Meadows in our own backyard, there are bass, bluegill, pike, pickerel and perch. Lake Whitingham also offers some ice fishing opportunities. There are also many contests and festivals that involve ice fishing in the winter months. (you’ll need to get a license for all fishing). There are some great ice fishing tips and locations here.
Various locations around Brattleboro
Road biking in the winter can be quite invigorating. Check out our summer guide for details on some great rides that start and end at the inn.
Magic Mountain (map directions to this location)
Magic Mountain (about 30 miles away, directly up Route30). Magic Mountain is where skiers and boarders seeking adventure can soar past their limits on some of Vermont’s most challenging and interesting slopes. Here at Magic, our sole purpose is to deliver an authentic New England skiing experience offering classic Vermont-cut trails in a relaxed, intimate and family friendly atmosphere. In offering southern Vermont’s best downhill skiing, riding and tubing terrain, we remember what original Vermont skiing was all about. So will you. With 40 trails broken down into 1/3 easy, 1/3 intermediate and 1/3 expert, there is something for everyone here. There are 4 lifts and a vertical drop of 1700 feet.
Mount Snow (map directions to this location)
Mount Snow (about 10 miles away, on Route 100 north of Wilmington) provides wonderful, challenging slopes with plenty of attractions both slopeside and in the immediate area. Mount Snow begins the 2007-08 season under the new ownership of Peak Resorts. Since April, Peak Resorts has invested over $6 million in the resort, including the purchase of 101 energy-efficient fan guns — giving Mount Snow the most fan guns of any resort in New England. There are 107 trails and 19 lifts with a vertical drop of 1700 feet. With 15% easy, 70% intermediate and 15% expert trails, there is something at Mount Snow for everyone.
Stratton Mountain (map directions to this location)
Stratton Mountain (about 35 miles from us).
Stratton Mountain means more runs, more snow and more fun with the ultimate in lift capacity, 90 percent snowmaking and the East’s No. 1 terrain parks (SKI Magazine). Stratton has 90 trails with 14 lifts and a vertical drop of 2003 feet. There are 42% easy, 31% intermediate and 27% expert runs, making this a great place for the beginning skier.
Memorial Park (Childrens) (map directions to this location)
Memorial Park in Brattleboro has a gentle and friendly slope available for the younger or first time skier. From our driveway head to the right (downtown) and make a right on route 9. Take route 9 to the covered bridge and make a left over the bridge. The park is right there.
Harris Hill Ski Jump (map directions to this location)
Each February ski jumpers from the world over compete at the Harris Hill Ski Jump. It is one of the few Olympic sized, 90 meter jumps in the U.S. The competition is held each year around the end of January or beginning of February. Read more about this unique piece of Brattleboro history here. The ski jump is just about a mile from the Inn, on Cedar Street.
Mount Snow (map directions to this location)
Home of the X Games and great snowboarding.
West Brattleboro VAST trail access
Snowmobiling in southern Vermont is becoming more and more popular. In West Brattleboro you can access the VAST (Vermont Area Snow Travelers) system of trails. Stop in at Vermont RV on Route 9 and speak to the folks there for more information. You can go west to Wilmington and north on route 100. There you have access to the same system of trails. You need to register with VAST. You can call 802-464-3284 or 802-254-4881 for information. There is an annual fee for registration with VAST.
Brattleboro Winter Carnival
Rumored to be the oldest ongoing winter carnival in the country. During the parade on the opening Saturday, enjoy sugar on snow, a unique delicacy in which hot maple syrup is drizzled across a dish of clean snow and served with pickles and doughnuts. If you’re looking for an authentic, small-town Vermont experience, you’ll love the Brattleboro Winter Carnival.