New England in Fall

A drive from Connecticut to Vermont reveals New England’s fall spectacle

Words and photographs Tess Paterson

We’re queuing for a take-out coffee on the main street of Brattleboro – a southern Vermont town on the Connecticut River. Way ahead of us is a teen with spiked hair in shades of jet black and orange. I glimpse an abundance of studded facial jewelry; a skein of elaborate neck tattoos. “Can I get a decaf skinny ginger-cinnamon macchiato with no froth?” she asks. Then pauses. “Or no, make that a spiced-pumpkin matcha chai latte? With a cranberry muffin on the side?”

Unfazed, the barista nods. They shoot the breeze, chat leisurely about the weekend ahead. I catch my husband’s eye, see the panic of an overdue caffeine fix. We wait. They greet a newcomer on a skateboard who clearly exited his bed about 30 seconds ago. All is deeply, utterly chilled. Several eons later we emerge with two flat whites to go. Happily, the legend of creative, offbeat Vermont seems pretty spot on.

Skinner State Park Massachusetts Buttermilk pancakes, Edson Hill VT Railway junction Kent CT

We’re driving up from Connecticut, crossing into Massachusetts and heading north for Stowe. It’s late October, and shopkeepers and waitrons insist that we’re cutting it fine. “You shouldda seen it two weeks ago!” they exclaim, perturbed by our lack of forward planning. “Columbus Day weekend? It was an absolute picture!”

Fortunately the southern part is still a blaze of multi-hued glory. Stopping at the Connecticut town of Kent is like blundering into a movie – white clapboard houses, quaint, not too-touristy stores, the ubiquitous overhanging power lines backed by countless glorious trees. All around are immaculate unfenced yards, cheery folk, an admirable lack of any introversion whatsoever.

Orange pumpkins are dotted about like a sort of mad Morse code

In tandem with the turning leaves, America’s deep love for festivities plays out in a monumental pumpkin display. This orange obsession begins in September, builds up to Halloween and culminates in late November with the blow-out that is Thanksgiving. Entire fields are dedicated to pumpkin photo-ops. They’re in windows, on walls, dotted about like a sort of mad Morse code. Pumpkin pie is a thing. And warming to the autumnal theme, taverns offer mulled wine with a shot of pecan whiskey; donuts are made with apple cider.

Bear sculpture Kent CT Fall colour Newfane VT The Village Butcher Woodstock VT

We meander through Woodstock, a pretty town that was charted in 1761. Not to be confused with Woodstock in New York (that eponymous peace-fest celebrated its 50th anniversary in 2019), it boasts some elegant architecture and worthwhile galleries. Like a magnet my Karoo-born husband heads straight for The Village Butcher, drawn to the smoky kielbasa sausages and homemade meatloaf. It’s a bakery too, famed for its vast cinnamon rolls. Stocking up on some leaf-shaped bottles of maple syrup, we carry onwards to Stowe.

Stowe is renowned for outdoor pursuits, from zip lining to nippy autumn weddings

A gem of the Green Mountain State, Stowe has a rep for being the best skiing territory in the eastern USA. It’s a multi-activity destination, perfect for hiking, snowshoeing, and all manner of outdoor pursuits from zip lining to nippy autumn weddings. Being further north and cooler, Vermont’s intense fall reds are making way for more coppery hues and gorgeous bare branches.

Stowe is big enough to have a good selection of restaurants and shops, small enough to retain a sense of New England charm. Our one big spoil is dinner at Cork, a beautifully pared down restaurant and wine bar. Owned by dynamo siblings Danielle and Katie Nichols, it’s got a superb seasonal menu and a cellar stocked with a host of natural wines.

October colour Newfane VT Kent CT indie book store Edson Hill Vermont Stowe Vermont

Of course Vermont is above all craft beer country, with more breweries per capita than any other state. Like every other ingenuous tourist we start with the Heady Topper, a local Stowe brew. Let’s just say that one review declaring it ‘piney, bitter, not pretty all all,’ summed it up perfectly for me. What I did enjoy was a taste of the Cream Puff War – a double IPA that’s not unlike a peach melba smoothie. Granted, not an everyday tipple, but it perked me up no end.

At the Trapp Family Lodge we ease into the retro Heidi vibe

We spend two nights at Edson Hill, a lovely inn with chic timber cabins and forever views. In between fabulous forest walks, we drive up to Smugglers’ Notch – a truly spectacular switchback pass with views across Mount Mansfield State Park. All around is autumnal loveliness – rich greens, neon yellows, smudges of grey. Heading back, it’s sundowner time at the Trapp Family Lodge. A chalet-style hotel, it’s owned by the descendants of the original Von Trapps who fled Austria for Vermont in 1938. Sipping on a dunkel lager and surrounded by spindle-backed furniture we ease into the retro Heidi vibe. It takes me a full week to stop humming ‘The Lonely Goatherd’ melody.

Timber barn Vermont Birch forest near Stowe

All too soon we’re heading back south, past Chelsea, Plymouth and Chester. Halloween is just days away. We see signs for Haunted House tours, stare transfixed at entire houses clad in gauzy spiders’ webs. An impressive number of patios boast life-size skeleton decor – perched on old sofas, draped over wine barrels, grinning maniacally from colossal pick-up trucks. As with the Zeppelin-sized Santas that appear in December, I’m wondering where on earth people store all this festive tackle.

At Newfane we check into The Four Columns Inn (currently under renovation). It’s got red Adirondack chairs on the stoep and a backdrop of low hills in radiant colour. We head straight into the woods, cross a narrow stream and savour fall’s fleeting phenomenon. The leaves are soft under foot, cushioning sound. All above is a canopy of back-lit gold.

Late fall, Kent CT Halloween decor Vermont Four Columns Inn Newfane VT

The inn’s cozy tavern sums up Vermont for me – genuinely friendly people, a relaxed atmosphere, properly good food. When the bartender asks a local resident what he did over the weekend, he takes a deep breath and says, “Well, I just retreated. Spent time with my dog, made apple sauce.” And so, fireside, we get chatting to strangers, swap stories, hear about local triumphs like the Gilfeather Turnip Fest where a tuber weighing 14,5 kg has just been declared the Grand Champion.

For Joburgers accustomed to a brief, if lovely autumn, New England in fall is mind blowing. Expect a mix of rare beauty, seasonal traditions, and an endearing sense of hippiedom. Next time I’d definitely stay longer.