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My mom, sister, and I braved more than 2,700 miles over 10 days to enjoy the start of autumn in New England.
October 16, 2025
We spent the last week of September driving through 12 states, visiting 2 national parks, and enjoying several B&Bs that we couldn't wait to cozy up in again.
Day 1: Johnny Appleseed and Pittsburg
Day 1: Johnny Appleseed and Pittsburg
Johnny Appleseed Festival (Fort Wayne, Indiana)
Johnny Appleseed Festival (Fort Wayne, Indiana)
Every September, my hometown hosts the Johnny Appleseed Festival. The colonial garb, antique booths, chicken and dumplings, and caramel apples have always been our favorite way to usher in the autumn season.
Pittsburgh
Pittsburgh
We spent the evening taking the Duquesne Incline up the mountain to enjoy the sunset and stellar nighttime city views, followed by some incredible pasta dishes at Dish Osteria Bar.
Where we stayed
Where we stayed
Kitschy B&B-style hotel
Breakfast: Self-serve breads/croissants, granola, yogurt, eggs
Day 2: Philadelphia
Day 2: Philadelphia
We got a quick history fix touring Independence Hall, the Liberty Bell, Betsy Ross' house, and Elfreth's Alley (the oldest continuously inhabited residential street in the US). Then savored some dumplings at Reading Terminal Market and a sampler of cheesesteaks from Jim's South St. The line went around the corner, but the Whiz cheesesteak was worth the wait.
Day 3: Sleepy Hollow and Newport
Day 3: Sleepy Hollow and Newport
Sleepy Hollow
Sleepy Hollow
Although we were a couple of weeks early for the spooky festivities and came through on a Monday when a lot was closed, we enjoyed walking around the cemetery to see Washington Irving's grave and the Old Dutch Church.
Newport, Rhode Island
Newport, Rhode Island
Newport was the quintessential coastal town—complete with a scrimshaw shop among the boutiques along Bowen's Wharf. We had the best (and probably only at $40 a roll) lobster rolls and clam chowder of our lives at the Newport Chowder Company, sharing a chilled New England roll and a warm Connecticut roll.
Day 4: Martha's Vineyard and Cape Cod
Day 4: Martha's Vineyard and Cape Cod
We only spent a night on Cape Cod, but enjoyed dinner and our quiet stay in a woodsy neighborhood in North Falmouth. Fortunately, our host told us we'd need about an hour to park and take a shuttle to the Martha's Vineyard ferry, saving us from trying to park right at the ferry 15 minutes before departure.
After a breezy, 45-minute ride to the island, we picked up our bike rentals a short walk from the dock and rode into Oak Bluffs to shop and see the whimsical Victorian gingerbread houses.
Day 5: Boston and Salem
Day 5: Boston and Salem
Boston
Boston
Another historic day exploring the Old North Church, Paul Revere's house and grave, Acorn Street, and multiple old graveyards. We had a great stay at Hotel Indigo, which was walking distance to a lot of what we wanted to explore in the city, and enjoyed a memorable dinner of elevated tapas and Baked Alaska at Yvonne's.
Salem
Salem
We visited just in time to beat the mobs of Halloween visitors. Cloudy weather created the perfect mood for exploring the witchy history and spooky spell shops of Salem before we continued up the coast.
Day 6: Acadia National Park
Day 6: Acadia National Park
We fortunately only had one rainy day on our trip—unfortunately, it was the day we visited Acadia National Park. The rain stopped long enough for us to hike the treacherous iron ladders of the Beehive Loop trail that took us along cliffs overlooking the park. We also paid to drive up Cadillac Mountain after hearing the rain would clear, only to be disappointed by endless fog.
Where we stayed
Where we stayed
Friendly stay in a quiet farmhouse
Breakfast: Maine wild blueberry pancakes, French toast, and eggs Benedict w/sausage and potatoes
Day 7: New Hampshire and Vermont
Day 7: New Hampshire and Vermont
New Hampshire
New Hampshire
Initially hesitant to extend our driving time, we were grateful to add a bit of time to coast along the Kancamagus Highway (Scenic Route 112), which gave us views of some much-anticipated fall foliage, river rapids, and covered bridges on our way to Cannon Mountain Aerial Tramway. We got even better views riding up and walking around the peak—enjoying a beer at the highest tap in New Hampshire after being spellbound by the sweet leaf and pine aroma that invigorated the mountain.
Vermont
Vermont
We continued through the beautiful autumn scenery, stopping at Sugarbush Farm for some delicious cheese and maple syrup samples before spending the evening in Brattleboro, where we ate dinner at the Royal Diner (a fun train-car-turned-diner experience) and had decadent maple and salted caramel twist ice cream at Nik's Creemees.
The next morning, we couldn't resist some great finds at the Wilmington Antique & Flea Market and Hogback Mountain Country Store.
Where we stayed
Where we stayed
Quaint historic charm
Breakfast: Pan-seared oatmeal w/cinnamon apples and French toast w/bacon
Day 8: Finger Lakes
Day 8: Finger Lakes
The parks of upstate New York alone were worth visiting, featuring impressive waterfalls along shady trails, but we also enjoyed driving around the stunning lakes to get to our favorite, most ornate house of the trip.
Where we stayed
Where we stayed
Luxurious, decadent Victorian house
Breakfast (changes seasonally): 3 courses of pear and almond oatmeal, asparagus eggs Florentine, and buttermilk pancakes w/strawberries and whipped cream
Day 9: Niagara Falls
Day 9: Niagara Falls
Niagara Falls
Niagara Falls
While the falls are impressive from above, the real fun was getting soaked (from the neck above, anyway, thanks to the notorious blue ponchos) on the Maid of the Mist boat ride.
Buffalo
Buffalo
We got a taste of Buffalo, which included Anchor Bar's famous wings and roaming around Burning Books, before heading down to our B&B to enjoy some lakefront views.
Where we stayed
Where we stayed
Tasteful, spacious w/Lake Erie views
Breakfast (changes daily): Breakfast casserole w/pumpkin English muffins and local pumpkin butter
Day 10: Cuyahoga National Park
Day 10: Cuyahoga National Park
Wandering through the towering, staggered rocks painted bright green from the sunshine-bathed moss of the Ledges Trail, followed by taking the short path to Brandywine Falls, was a great way to end our ultimate New England road trip.
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