Three Fall Foliage Towns Off the Beaten Path

With its charming downtown, great restaurants and wonderful fall colors, what’s not to love about Simsbury, Connecticut? Plus, there are great hiking, biking, and boating in the fall.Connecticut Office of Tourism

Simsbury, Conn.

Located just outside Hartford, Simsbury is listed on the National Trust for Historic Preservation as one of its ‘Dozen Distinctive Destinations’. It has charm to spare, including a downtown filled with historic homes and great restaurants. Soaring above Simsbury is one of the best places to take in the splendor of autumn: the 165-foot Heublein Tower, built for the Heublein family (creators of A.1. Steak Sauce), atop of Talcott Mountain.

Located in Talcott Mountain State Park, the 1,000-foot tall Talcott Mountain offers views of 1,200 square miles on a clear day, they say. There’s New Hampshire’s Mount Monadnock, 80 miles away, and the Berkshire Hills to the northwest. That thin blue band to the south? This is Long Island Sound. All of these stunning landscapes are enveloped in the fiery hues of Mother Nature. And did we mention the Tower Trail is only 1.25 miles long? At the base of the mountain, the Talcott Collective ( offers disc golf, food trucks and craft beer, as well as live music.

A mere weekend is not enough time to have fun here. For serious hiking, the blue-marked Metacomet Trail runs the length of the city. By bike, the Farmington Canal Heritage Trail ( rewards cyclists with a colorful and easy tour (and free bike rentals for visitors). At the water’s edge, the Farmington River offers both flatwater and whitewater paddling; rentals are available at Collinsville Canoe & Kayak ( near Collinsville. The Old Drake Hill Flower Bridge is another fun destination for a fall hike. Inspired by our very own Flower Bridge in Shelburne, this former 19th century truss bridge-turned-walkway/bike path is ornately adorned with flowers.

For a room with a view, try the 98-room, two-story Simsbury Inn (; from $179). And don’t leave town without paying homage to Connecticut’s tallest and oldest tree, the Pinchot Sycamore, at Pinchot Sycamore Park on Route 185. The goliath tree, 106.8 inches in diameter, is said to have about 400 or 500 years old.

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Besides the amazing fall foliage, Walpole, NH has a sweet secret: it’s the mothership of chocolatier LA Burdick. Don’t miss a stop at their store if you’re in the area.Diane Bayer

Walpole, NH

Home to around 3,700 residents, including filmmaker Ken Burns, this pretty village is located in the southwest corner of the Granite State, pushing Vermont. Driving north on NH Route 12 reveals plenty of color, a glimpse of the glories to come. “Drive to Hooper Golf Course or Alyson’s Orchard. The views are fabulous,” said sculptor Philip Morgan of the Walpole Artisan’s Cooperative. “You drive up the hills overlooking the Connecticut River Valley, and, wow!”

After buying blueberry soap from the co-op (, we took his advice and walked up the winding hill to Alyson’s Orchard (450 acres) ( This pick-your-own farm stand (named one of America’s Top 12 Orchards by Travel + Leisure) was bustling with families, visiting resident goats and filling billing baskets with apples (they grow more than 50 varieties here).

These kids are cute, but if Walpole had a mascot, it would be a little chocolate ganache mouse with toasted almond ears, sold at LA Burdick ( Walpole is the original location of this exquisite chocolate shop, founded by chocolatier Larry Burdick. The mice are made by hand for three days, a few kilometers from here. On a chilly fall day, Burdick’s famous drinking chocolate is the perfect treat. And Burdick’s namesake cookie is so good, “It would make Mrs. Fields cry,” said our mate, Paul.

All that puffing is sure to make you hungry. In Walpole, NH, go hearty with a thick sandwich or large salad from the farmer-owned Hungry Diner.Diane Bayer

Adjoining the Main Street Chocolate Factory is The Restaurant at Burdick’s (; entrees from $26). Co-owned by Larry and Paula Burdick and Ken Burns, the French-American restaurant is a local gathering spot (try Ken’s Salad, the filmmaker’s own creation). South of town, the Hungry Diner ( is a farm-to-table restaurant with food sourced from their own farms in the Walpole Valley. The casual restaurant offers indoor and outdoor seating, 16 craft beers on tap, delicious edibles such as Korean BBQ Beef Salad ($17), and absolutely killer blueberry milkshakes.

There are some good hikes nearby (the Mount Kilburn Trail is a favorite), but the main draws are the colorful views and small-town feel. Located steps from the first tee of the Hooper Golf Course, c.1788 Watkins Inn & Tavern (; from $190) features four bedrooms and period details such as wide plank floors and old stencils. The new owners (as of January 2021) have added some updates. But in the fall, “it’s all about the view!” says co-owner Eric Brandolini.

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Could there be anything more “New England” than a covered bridge in the fall? We think not. Montgomery, Vermont has several, including this one, Comstock Covered Bridge.Vermont Department of Tourism

Montgomery, Vermont.

Covered bridges and country inns? It doesn’t get more “picturesque New England” than that. Add crimson and gold mountains to the mix and it’s Instagram heaven. This is the attraction of little Montgomery, 1,184 inhabitants. High up in the Northeast Kingdom, near the Canadian border, the “Covered Bridge Capital of Vermont” has six of these bridges within the city limits. There is another that straddles the city limit with Enosburg. That’s more covered bridges than any other city in the United States, they say, thanks to Montgomery’s unique geography.

A Bridge Tour (there’s a list and directions on the city’s website) is a great way to get familiar with the area. If you’re a skier, you might already be familiar with Montgomery, thanks to the nearby Jay Peak Resort. Big Jay, a 3,786-foot high spur of Jay Peak, towers over the northeast corner of the city. The Jay Peak Tramway (; $20; daily through October 10), an aerial tram, is a fun way to see nature’s handiwork, with sweeping views of Vermont and the Quebec. Canoeing and kayaking the Northern Forest Canoe Trail is another active option. Back on land, explore the network of hiking trails at Hazen’s Notch, maintained by the Hazen’s Notch Association (, best enjoyed while munching on a crisp apple from a local farm stand.

Speaking of food, locals will direct you to Bernie’s Restaurant (802-326-4688;, named for chef John Boucher’s wife, Bernadita. They offer all-day dining and evening specials (tex-mex, prime rib, roast turkey). For dinner, the INN Restaurant at the INN on Trout River (802-326-4392;, open Thursday through most Sunday nights, is a great place to try, for example, the Bambi burger (venison; $25) or ostrich steak ($42). The inn itself offers 11 rooms in a Victorian house and carriage house, with rates starting at $204. Meanwhile, the Circa 1880 Phineas Swann Inn & Spa (802-326-4306;; from $139) feels very Vermont, with its four-poster beds, antiques, and fireplaces. The 10 rooms are located in a river house, a carriage house and the main inn. In addition to the main hostel, this B&B is dog friendly.

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Diane Bair and Pamela Wright can be contacted at [email protected]


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