Bennington - A Perfect Gateway to New England

My favorite spot in Bennington is the Old First Church situated on Monument Avenue in Old Bennington, the original village from which the town grew. The church itself was built in 1805, although the site has been home to a church and cemetery since 1762. Any bride-to-be who may have dreamed of a white wedding would be hard pressed to find a more perfect location for her ceremony.

The white timber-framed colonial building sparkles in the sunlight, and looking at this stunning piece of New England architecture as you drive into Old Bennington, it is easy to understand why it was designated Vermont's Colonial Shrine in 1937. Inside the building, the huge glass windows allow the light to flow in from all directions. On the ground level, there are no pews, but "boxes" that kept families together in worship. Pews upstairs took care of the overflow, and today you can still see the handiwork of bored schoolboys carved into the wooden sideboards. The church is magnificent in its simplicity and exemplifies the best in colonial architecture.

Quick Tips:

While at the church, take the time to walk about the cemetery. The graves of some of Old Bennington's earliest residents lie alongside Revolutionary and Civil War soldiers, state senators and a good number of former state governors.

The cemetery's most famous permanent resident is Robert Frost, who is buried here alongside his wife and children. Frost lived for a time just north of Bennington, and from his gravesite, you will have a wonderful view of the valley and mountains beyond.

Grey gravestones sit quietly amongst towering maples, brilliant in their autumn color, and provide all who visit with a chance for peaceful reflection.

Best Way To Get Around:

Leave your car parked in front of the church and walk up Monument Avenue toward the Bennington Battle Monument. On both sides of the maple-lined street (ablaze in color during the fall) are some of the oldest homes in southern Vermont, several of which are over 200 years old. These are beautiful examples of antique clapboard homes, some of which have been painstakingly restored and are fine reminders of our colonial heritage. The dates of construction of most of these houses, along with their original residents, are indicated on wooden plates outside each home.

At the top of the hill is the Bennington Battle Monument, commemorating a 1777 colonial victory over the British at the Battle of Bennington. From the lookout in the monument you can see all of Bennington and the mountains that surround it. A short, pleasant walk down the hill brings you back to the church, from which point you can explore other interesting sites in the area.

June usually signals the start of numerous arts and crafts fairs and antique shows in towns and villages in the Bennington area. About 20 minutes north of Bennington is the town of Manchester, and the meadows behind Hildene is the primary site for many fairs that take place throughout the late spring, summer and fall seasons.

Everything from bric-a-brac to quality colonial antiques can be found at these fairs, but don't expect a bargain. Vendors generally know their antiques and crafts here and quality items will put a dent in your wallet, but you'll still do much better here than you would on the Upper East Side of Manhattan.

These art and antique fairs are repeated throughout some of the loveliest villages in New England, including Dorset, Weston, Newfane, and Grafton. Nothing compares to spending a leisurely sunny afternoon mingling amongst a friendly crowd, in beautiful surroundings, and topping it off by finding that special something that goes perfectly in your front room.

Pick up a Friday copy of the Bennington Banner, which generally lists fairs in the area, or check out the Vermont websites for upcoming events. A good one is click here,, which lists activities of all kinds in the Manchester and Bennington area.

Heading south for 20 minutes from Bennington on Route 7 will bring you to the Vermont-Massachusetts border and Williamstown, the home of Williams College and some of the most privileged college students in the country. Williamstown is a quintessential college community, with a small town center catering mainly to the tastes and budgets of its students.

During the summer, however, when most of the students have gone their separate ways, Williamstown becomes a favored destination for theater lovers who look for entertainment beyond Broadway. They find great satisfaction here every year, when the Williamstown Theater Festival stages about 10 plays between mid-June and the end of August, each play running for about two weeks in two separate theaters. These are not amateur productions, but programs that are as good as anything seen off Times Square and starring household names in the world of entertainment. Alumni of the WTF include Gwyneth Paltrow, Olympia Dukakis, Richard Chamberlain, Mary Tyler Moore, Rita Moreno, Kevin Bacon, Joanne Woodward, Marisa Tomei, John Lithgow, Sigourney Weaver, Ethan Hawke, Stockard Channing, Alec Baldwin, Christine Lahti, Richard Dreyfuss, Raul Julia, Bernadette Peters, and many, many more actors who have made Williamstown their home for a few weeks each summer.

The only way to obtain tickets is by filling out an application form, which you can obtain by calling the WTF offices at 413-597-3399. Brochures are mailed out on May 1 and this is the only way to obtain tickets before the season begins in June. A hint for those who really want to attend: Become a "Friend of the Festival" by making a minimum contribution of $100, which will get you a brochure in advance of the May 1 mailing date, and a much better chance for those coveted tickets. Don't regard this as a bribe, but more of an "agent's fee" that will assure that you get some of the hottest tickets in summer New England. Be warned--the shows are always sold out.

The center of downtown Bennington is "Four Corners", where Route 9, running east from New York through Vermont and on into New Hampshire, meets Route 7, which runs north from Connecticut and Massachusetts up through Vermont. This is Bennington's commercial heart and the center of one-off specialty shops that visitors will enjoy visiting.

One shop that gets missed more often than not is Katie Cleaver's tiny (and I mean tiny) outlet on Route 7 heading west toward New York. Located close to Four Corners, and next to the Left Bank gift gallery, this is The Women Of Bennington's best kept secret. I would challenge anyone to find a woman in the area who hasn't purchased one of Katie's finely crafted silver and/or gold creations for herself, or as a gift for others.

The shop is so small, it is easy to walk by it without really noticing it. Katie doesn't make it any easier by opening her shop only three days a week, from Thursday through Saturday. The rest of the week is spent working on her stock, which by closing Saturday is pretty much depleted. Those in the know realise that you have to get to her shop on Thursday morning for the best selection.

Katie's creative gift is enough reason for anyone to stop by her shop, but there are others. I have brought friends from New York and California who have literally gone slack-jawed at the quality of Katie's work, particularly in light of the prices that she charges for it. I have told Katie that she could increase her prices 50-100 percent and still sell her entire stock, but she will not.

That is yet another reason to stop by. Katie is one of the most charming individuals you will ever meet, a genuinely nice person who could not bear to increase her prices for her loyal clients who have become her friends. The fact of the matter is that Katie probably doesn't need your business. In selling everything she makes, she is happy doing what she is doing, on her own time and in her own fashion. Still, that doesn't mean that you shouldn't stop in to meet one of a dying breed of individualists in New England. You'll love chatting with her, and even if there is only one piece of jewelry left in her display case, chances are that you will probably walk off with it.

Take a trip up Historic Route 7, the old picturesque two-lane highway that runs from Bennington through Shaftesbury, Arlington, and Sunderland and on to Manchester. Just north of Shaftesbury is a little unpainted barn on the left hand side of the road that acts as the workshop for David and Patty Herzfeld, proprietors of Bottum Hill Studio. David is a talented artist, equally at home in making beautiful hand-crafted custom furniture as he is in drawing and painting. Patty specialises in pottery, and both are becoming increasingly popular amongst locals and visitors alike.

Continuing north, you will come to Arlington and its attractive village center. You may find an old book sale going on at the local library, a bake sale at the local church, or a student car wash at the local gas station. This is very much small town America and a pleasant place to stretch your legs.

North of Arlington, keep your eyes peeled for Christmas Days, a specialty shop run by Andrew and Linda McKeever. I was never one for Christmas stores in the summer, but those seasoned shoppers and credit card addicts that I know swear by this shop.

You are now entering Sunderland territory. Look for the little gift shop across the highway from the basket store. This shop carries without a doubt the creamiest, richest home-made fudge you will find anywhere in Vermont. And what a variety. You can't go wrong with the chocolate walnut (the cure for my chocolate cravings), but try some of their specials as well.

If you are looking for something as rich but a bit cooler, just up the road is Wilcox Dairy, a supplier of dairy goods to the local southern Vermont community. A dirt road takes you to the dairy itself, currently rebuilding after a fire devastated the old wooden barn. It also takes you to a little wooden hut which sells fresh, homemade ice cream. Sitting on a bench in a dairy farm off the main highway, with the sun in your face, country air in your lungs, and a praline and cream cone in your hand--it can't get better than this.

Just past the dairy is the family-owned Equinox Valley Nursery. Even if you're not in the market for plants, this is a fun, friendly stop, especially during October, when the nursery goes all out with a fall and Halloween theme that attracts thousands of families from throughout the Northeast.

Manchester itself is home to dozens of exclusive factory outlet stores eager to relieve you of your cash. Save it for Al Ducci's Italian Pantry on Elm Street. Al has a egg plant parmesan that would make even die-hard Italian-Americans weep. It's a bustling place, especially around the lunch hour, and most of the good stuff, including their breads, is gone by mid-afternoon, so get there as early as you can.