After a peaceful night in Saratoga Springs, it was time to move east and head for Boston — our final major stop on the East Coast USA and Canada road trip. The morning air was crisp, the sky bright, and the trees were beginning to show their first hints of autumn colour. We hit the road around 9 a.m., fuelled by caffeine, curiosity, and the excitement of crossing through yet another state.
Leaving Saratoga Springs
We grabbed coffee and pastries from a roadside service station in Stillwater before taking the backroads through Hoosick Falls and into Vermont. The scenery was absolutely stunning — winding roads cutting through golden fields and forests brushed with red, orange and amber. Every corner felt like a postcard waiting to happen. We followed quiet highways through Bennington and Wilmington, where the trees arched overhead and sunlight filtered through like a stained glass window of autumn hues.
Wildlife and Winding Rivers
Despite the many road signs warning of moose, we didn’t spot any — just a group of wild turkeys wandering around a cemetery in Jacksonville. From there the road wound alongside a broad, sweeping river, perfectly reflecting the colours of the trees above. It was peaceful, relaxing, and one of the prettiest stretches of driving on the entire trip.
Perfect Coffee Stop – Shelburne Falls
By late morning we reached Shelburne Falls and stopped at the Shelburne Falls Coffee Roasters & Bakery — one of the best finds of the trip. The smell of roasted coffee hit us before we even stepped inside. We ordered two of the best lattes we’ve ever had — a Maple Toffee Latte and an Apple Cider Donut Latte — along with toasted sandwiches that were nothing short of incredible. I had the Figgy Piggy (Prosciutto, Brie, Fig Jam, Dijon Mustard, and Greens on Multigrain Bread), and Deb went for a BLTA (Bacon, Lettuce, Tomato with Smashed Avocado and Mayo). Both were outstanding and come highly recommended if you ever find yourself in the area.
Through New England Towns
From Shelburne Falls, the roads gradually widened as we dropped down into Massachusetts, passing through Greenfield, Erving, and Templeton. The towns carried familiar names — Leominster, Tewksbury, Woburn — a reminder of just how many English settlers once called this part of the world home.
Stopping in Salem
We pulled into Salem in the early afternoon, a place we’d both been really looking forward to visiting. Unfortunately, it didn’t quite live up to expectations. The town is famous — or infamous — for the Salem Witch Trials of 1692, when 19 people (14 women and five men) were executed after being accused of witchcraft. Another 150 were imprisoned, and one man, Giles Corey, was pressed to death for refusing to plead. The tragedy has become a defining part of Salem’s history — but what we found felt more like a theme park than a memorial.
The streets were filled with witch-themed souvenir shops, costumed tour guides and Halloween decorations. We visited the Witch House (actually the home of Judge Jonathan Corwin, who presided over the trials), wandered through the cemetery where the Salem Witch Trials Memorial honours the victims, and took the obligatory photo with the Bewitched statue. Despite the history, it all felt oddly commercialised and a little disrespectful — more Disney than documentary. Even Gallows Hill, where the hangings supposedly took place, has been turned into a visitor stop complete with spooky displays.
Heading into Boston
After leaving Salem, we rejoined the highway towards Boston. It was rush hour, and traffic crawled through industrial areas and across bridges before disappearing into the maze of tunnels that feed into the city. Naturally, we took a wrong turn coming out the other side and added a bonus 20-minute detour to the day.
Checking In – The Omni Parker House
We finally arrived at the Omni Parker House Hotel just as the sun was setting. There was a brief moment of confusion — no doorman in sight — so Deb dashed inside to ask where we could leave the car. A few minutes later a valet appeared, handed us a ticket, whisked the car away, and helped us inside with our bags. Check-in went smoothly, and we learned a little more about the hotel’s history: it’s the birthplace of the Boston Cream Pie and has hosted the likes of Charles Dickens, John F. Kennedy and Malcolm X over the years.
Despite its impressive past, the hotel didn’t have quite the same sparkle as its Toronto namesake. Our room was the smallest of the trip but comfortable enough for a couple of nights.
First Impressions of Boston
By the time we’d unpacked and changed, it was late and many nearby restaurants were closing. We wandered the streets expecting a lively city centre, but most places had already shut their doors. In the end we retreated to the hotel bar for a couple of beers, some bar food, and — naturally — a slice of Boston Cream Pie. Not quite the grand introduction to Boston we’d imagined, but still a sweet ending to a long day on the road.
Next Up
Tomorrow we’ll be exploring Boston properly — walking the Freedom Trail, soaking up the city’s history and culture, and seeing if it can redeem itself after our slightly underwhelming first impressions.
