Some trips stay with you forever — the kind that feel like stepping into a living painting. Our fall road trip through Vermont in 2022 was exactly that.
Every autumn, the Green Mountains ignite in deep reds, glowing ambers, and brilliant golds. The colors stretch across rolling ridges, quiet valleys, and winding country roads, creating one of the most breathtaking fall landscapes in North America. But what made this journey truly unforgettable was experiencing it with our dog, Chance.
Traveling slowly allowed us to notice the little moments — mist rising over mountain lakes, covered bridges framed by crimson maples, farm stands overflowing with fresh cider, and quiet forest trails where Chance could explore beside us.
This 13-day dog-friendly road trip itinerary is built around the philosophy of slow, intentional travel. Instead of rushing between destinations, we embraced scenic detours, local discoveries, and eco-conscious choices that support small Vermont communities. Along the way, you’ll explore charming mountain towns, hike leaf-covered trails, visit historic villages, and experience the magic of fall foliage across Vermont and the nearby Adirondack Mountains.
If you’re dreaming of a road trip where nature, cozy small towns, and dog-friendly adventures come together, this itinerary will help you experience the Northeast at its most magical — one scenic mile at a time.
Day 1: Poughkeepsie, NY – Waiting Out the Storm [Detour]
On the morning of our our roadtrip from NYC toward southern Vermont, we were near the eye of a big hurricane. Instead of pushing through, we decided to stay a night in Poughkeepsie (~5 hours from NYC, ~4 hours to southern Vermont).
- Stay: Homewood Suites – Hilton (~$250/night)
- Dinner: Mahoney’s Irish Pub & Steakhouse – Bonus: it’s dog-friendly indoor seating and welcoming sign at the door that allows well behaved dogs!
The food was phenomenal! We enjoyed shepherd’s pie with a side of French onion soup, crispy fish & chips and buffalo wings. Friendly service and a first-night detour.
Day 2: [Travel] Drive to Jamaica, Vermont – Tiny Cabin Retreat
Check-out was at 11 a.m.—perfect timing to hit the road. With most of the heavy rain shifting west, our foggy drive included a quick stop at the Columbia Country Marker to stretch our legs. Just minutes into Vermont, we spotted wild turkeys crossing a quiet dirt road, a charming welcome to our adventure!
We checked into Apple Blossom Cottage, a tiny dog-friendly cabin with a fire pit and huge outdoor yard.
- Lunch: Rocky Hill Country Store – homemade sandwiches and fresh salads. Pick up some extra supplies for the evening and was told they do special pizzas every Wednesday night – preorder/prepaid for later pickup.
- SCENIC DETOUR – Sightseeing: Hermitage Road Covered Bridge – classic restored Vermont covered wooden bridge that’s part of The Hermitage Inn which is up the road.
- Evening: Campfire + pizza from the local general store
Our tiny cabin was full of charm—even with drafty nights, soft beds, and low water pressure. The real highlight? A huge outdoor space and unlimited firewood. We spent the chilly 60°F evening around the campfire, unplugged but still connected with fast WiFi for a few morning meetings.
Chance loved having space to zoom around after our long drive, and we woke up to bunnies, roosters, and woodpeckers—a nature-filled 7 a.m. alarm! This little cabin stay was the perfect mix of unplugging, cozy comforts, and outdoor adventure.
Day 3: Jamaica, VT – First Hikes & Covered Bridges
- SCENIC DETOUR – Start your day at the Jamaica Covered Bridge and enjoy a 2.5-mile hike to Salmon Hole in Jamaica State Park.
- For lunch, cozy up with soup or a sandwich at West River Provisions.
- In the afternoon, hike 2 miles to Lye Brook Falls in Manchester, then browse local treasures at the Manchester Flea Market in Adams Park. Wrap up with outdoor dining at Gringo Jack’s—the food wasn’t amazing, but the vibe was perfect for relaxing.
This day in Manchester and Jamaica perfectly blends scenic hikes, charming local spots, and laid-back dining. Whether you’re exploring waterfalls, strolling through flea markets, or simply enjoying the outdoors, it’s a relaxing escape that captures the best of Vermont in a single day.
Day 4: [Drive] Drive from Jamaica, NY -Saratoga Springs, NY [Detour]
- Day Highlights – Jamaica, VT to Malta, NY (1 hr 30mins)
Morning: Check out of your tiny cabin in Jamaica, VT and drive toward Malta, NY. - Lunch: [SCENIC DETOUR] Stop at 📍Workhorse Café in Windfall, VT, and enjoy a meal outdoors—perfect for soaking up the fresh air.
- Afternoon: [SCENIC DETOUR] 2.5-mile hike at 📍Lake Shaftsbury, VT to stretch your legs and enjoy nature.
- Evening: Check into your hotel in Malta, NY, and end the day with a late dinner at Panera (outside hotel) —soup in a bread bowl is the ultimate comfort after a day of travel.
Note: Due to Vermont peak foliage price gouging and limited dog-friendly accommodations in the Northeast Kingdom, we detoured to Saratoga Springs. We’ve never been and since there was an annual outdoor food festival that weekend we decided it would be a fun detour.
$$$ Tip: By staying in Malta we saved over $1400 that weekend (2 days); [the most expensive weekend anywhere in Vermont]. This detour saved us both money and stress (less crowds) while keeping the trip dog-friendly. We stayed at Home2suites in Malta for the weekend.
Day 5: Exploring Saratoga Springs + The Annual Saratoga International Flavorfeast
A Fun-Filled Day in Saratoga Springs
Day Highlights:
- Start the day 📍Saratoga International Flavorfeast – A celebration of global flavors from France, China, Japan, Italy, Mexico, America, and more. Cash only, arrive early; some favorites sell out fast!
- Shopping:📍Saratoga Saddlery – Browse iconic cowboy boots and local shops on Main Street.
- Thristy? 📍Gaffneys – Refresh with beer or cider by the outdoor fire pit (dog-friendly).
- Lunch📍Comfort Kitchen – Cozy, dog-friendly lunch with indoor hallway seating.
- Afternoon stroll 📍Saratoga Spa State Park – 1-mile stroll, pumpkin displays, and the scenic Avenue of the Pines—perfect for fall photos.
From sampling global dishes at the Flavorfeast to strolling through charming shops and scenic parks, this day in Saratoga Springs was a perfect mix of food, fun, and fresh air. The dog-friendly stops made it even better, and the vibrant fall scenery added the perfect backdrop to our adventure.
Day 6: [Drive] Malta NY. to Burlington VT.
A Scenic Drive to Burlington, Vermont
Day Highlights:
- [SCENIC DETOUR] Cute Farm stand📍Pattie’s Patch – Whitehall, NY – Stop at the orchard for fresh apples and a quick snack near the car.
- [SCENIC DETOUR] The colors!📍Orwell, VT – Drive through charming landscapes, snapping photos of the countryside and local church.
- Lunch: 📍 Orwell General Store – Grab a smoked ham sandwich and enjoy it in the car for a casual, scenic meal.
- Check into the hotel – This is our most comfortable 2 night stay of the trip! A huge 2 room suite with a king bed and kitchenette. 📍Green Mountain Suites – Large suite with firm king bed with a separate kitchenette and living room, stove, fridge and microwave – perfect to making homemade meals for Chance and humans.
- Dinner: After a few days of takeout it was nice to make a simple dinner back at our hotel room. Went to 📍Trader Joe’s about 10 min drive from the Hotel. Keep it simple with soups and salads for a cozy night in.
Conclusion:
This day was all about the journey—stopping for fresh apples, capturing Vermont’s scenic beauty, and enjoying simple, cozy meals along the way. Ending the day at Green Mountain Suites made it even better, with a comfortable bed and roomy kitchenette to unwind and recharge for the next adventure!
Day 7: Burlington, VT.
Most Dog-friendly town in Vermont
Exploring Burlington, Vermont
Day Highlights:
- Grab Breakfast at the Lodge (included with stay- but ends at 8am) – Start the day with a hot continental breakfast before heading out! (Chance was allowed in the dining area)
- [Photo] Parked the car📍Municipal Parking Lot – Offers high vantage points for sweeping views of downtown Burlington.
- [Photo] Walk aroung the 📍Historic Church Street – Stroll the charming pedestrian street full of shops and local character.
- [Photo] Take some photos 📍City Hall – Snap a few photos of this iconic building.
- Lunch at 📍 The Friendly Toast – We got ried chicken sandwich and big eggs breakfast; dog-friendly indoor dining makes it easy to bring your pup along.
- [Photo] After lunch walk towards the water 📍Battery Park – Take in scenic views and a relaxing walk.
- [Photo] We loved the the views from the 📍Waterfront & Burlington Waterfront Boat Ramp – Perfect for strolling and watching boats on Lake Champlain. On a clear day they say you can even see Canada! One of my favorite spots in town to people/ boat watch!
- [Photo] Thirsty? No visit to Burlington VT is complete without tasting a few craft breweries for any Beer connoisseur like dogdad! So we visited 📍Citizen Cider – Linh love cider, so had to add this spot to our list too! Cold cider outdoors with beautiful surroundings.
- This is one of Joe’s favorites 📍Zero Gravity – We got a few flights and full sized beers – Enjoyed the large outside patio while taking in the vibe.
- Grab late night bites at 📍Burlington Beer Co –[Dogs are only allowed in the outdoor patio / Indoor dining for service animals only] Got the cheese curds, meat plate, and pickles.
Conclusion:
Burlington is a perfect blend of city charm, lakefront views, and dog-friendly spots. From historic streets to waterfront strolls, and ending with casual bites and local brews, this day captures the essence of exploring Vermont’s vibrant downtown.
Day 8: Smuggler’s Notch & Stowe – Peak Fall Foliage Colors
A Scenic Day in Smuggler’s Notch & Stowe
Day Highlights:
- Arrive early! Driving to 📍Smuggler’s Notch – Start the day with a late morning drive through this dramatic mountain pass surrounded by towering cliffs and winding roads!
- Park off the side of the road a couple time to grab photos of the landscape. (only small cars can do this) By 1 PM we park in the small parking lot (almost filled up)📍Smuggler’s Notch State Park – to explore more of the park and take in the crisp mountain air. We were able to climb up to a high vantage point. Chance was like an agile mountain goat hopping up the mountain! Hike: Moderately difficult, wear hiking boots!
- Lunch: We wanted to grabbed lunch in town of Stowe – This is peak fall season and in Stowe (Woodstock) there’s lots of traffic and after three closed spots with no food service, we finally grabbed sandwiches to-go from a small takeout shop! .
- [Photo]📍Stowe Community Church Overlook – Capture postcard-worthy views of the iconic white steeple framed by the mountains from a further vantage point.
- [Photo]📍Stowe Covered Bridge – A classic New England landmark, perfect for photos.
- Around 4 PM we drove away from the crowds and decided to explore📍Sunset Rock during golden hour – a easy hike up for sweeping views of Stowe glowing with peak fall colors! [Hidden Gem]
- [Photo]📍Stowe Community Church (Close-Up) – Another look at this picture-perfect church right up front!
- 📍Shaw’s General Store – Picked up magnets and local maple syrup to remember the day.
- 📍Sunset Drive back to Burlington – Ended the day with a colorful drive back as the sky lit up with evening hues.
Conclusion:
From winding mountain passes to peak foliage views, Stowe delivered the quintessential Vermont fall experience. Despite the lunch hiccup, the mix of small-town charm, local shops and scenic overlook a hidden gem that made it one of the most memorable days of the trip!
Day 9: [Drive] Montpelier + Brookfield – Eco Cabin Stay
Day Highlights:
- Check Out – 📍Green Mountain Suites – Left Burlington behind on a sunny morning.
- Afternoon: On the way out of Burlington – in Williston, grab a quick bite at 📍GoodWater Brewery – Relaxed outdoor dining with a falafel salad and smashed burgers.
- Drive to 📍 Brookfield (An Eco Cabin/ working little farm- we’ll be staying for the next 2 days) – Scenic roads through small towns and rolling hills.
- [Scenic Detour]📍Montpelier, VT – Sightseeing at the Vermont State Capitol and exploring downtown. (1 hour)
- Grabbed a few rolls for take out📍Pho Capital – Vietnamese spring rolls and summer rolls; outdoor seating available for dogs.
- Check into Airbnb – Eco Cabin on a working farm in Brookfield, VT. Hosted by Jyl & Marc, with Sage (their friendly English sheepdog)
- Composting toilet with limited running water, high-speed WiFi, and friendly farm animals
- Met 3 retired Arabian horses, saw sheep, and heard the chickens
- Campfire at night! A nice treat to see the stars at night!
🌿 Conclusion & Takeaways
Staying at the eco-cabin in Brookfield was one of the most grounding experiences of our trip. It reminded us why slow, sustainable travel matters—choosing places that honor the land, respect resources, and allow you to truly connect with the community (and sometimes even the farm animals!).
Brookfield was a change of pace from the busier towns, and it gave us space to reset before the next leg of our journey. If you’re planning a Vermont road trip, we highly recommend adding an eco-stay to your itinerary—it makes the adventure feel more intentional, memorable, and connected to the heart of Vermont.
Day 10: Town of Woodstock + A magical detour
Day Highlights
Drive to Woodstock
- Wood Covered Bridge [Photo]
- Built in 1969, it’s one of Vermont’s most charming covered bridges, spanning the Ottauquechee River.
- Still open to vehicles, it’s a favorite photo spot right in the heart of Woodstock.
- Woodstock Inn
- A historic luxury hotel dating back to the 1800s, known for its classic New England charm, sprawling lawn, and elegant white façade.
- Even if you’re not staying, it’s worth stopping by to admire the architecture and gardens.
- Jenne Farm Road – Redding, VT – [Photos]
- Lucky for us, we came here right after the morning rain around 12:30pm and had the entire road to ourselves by luck for 30-40mins. The spot quickly filled up of 5-6 cars that came through when we left.
- FYI: this is a private farm and public road. Don’t block the road, drive on the grass, leave trash and be disruptive. Over the years, we heard this spot is closed off due to Instagram.
- We were here for about 30 mins because it was empty. Even got to walk up the road with Chance with no cars. It was a true bucketlist moment to shoot here with Chance! (Cover pic)
- Known as the most photographed farm in New England, Jenne Farm has appeared on calendars, puzzles, and in the movies Forrest Gump, Bud Light and Funny Farm.
- Its red barns, dirt road, and rolling hills make it the quintessential Vermont fall scene!
- Lucky for us, we came here right after the morning rain around 12:30pm and had the entire road to ourselves by luck for 30-40mins. The spot quickly filled up of 5-6 cars that came through when we left.
- Woodstock General Store – grabbed bread, water, and local beers (car snack)
- Brookfield Floating Bridge [IPhoto]
- Built in 1820, it’s the only floating bridge east of the Mississippi River, spanning Sunset Lake on pontoons.
- Modern updates use FRP pontoons, but the timber deck preserves its historic look.
- Removed each winter and reinstalled in spring—a true testament to Vermont’s community spirit.
- Stove fire at the eco-cabin
- DINNER – homemade at the cabin (local sausages, bread, and salad)
🌿 Conclusion & Takeaways
This day felt like a postcard come to life—quaint covered bridges, the iconic Woodstock Inn, Jenne Farm’s cinematic scenery, and Brookfield’s one-of-a-kind Floating Bridge. We ended the night in true Vermont style: with local food, a outdoor campfire, and a little stove fire inside the comfort of our eco-cabin.
Day 11 Brookfield → Troy, NY
Day Highlights:
- Check out of eco-cabin in Brookfield, VT → drive to Troy, NY
- Drive to Troy for rehearsal dinner
- LUNCH – on the road
- DINNER – rehearsal dinner with family & friends
Day 12: Wedding Day in Troy
[Detour] 📍Troy, NY
- Brunch at Little Pecks – cozy café with great coffee and casual bites
- Troy Farmers Market – one of the best in upstate NY, packed with local produce, baked goods, and artisan finds
- Troy Sign – don’t miss snapping a pic at this iconic city spot!
- Franklin Alley – popular hangout lined with colorful street art, perfect for a quick stroll
Get ready for the wedding of our friends Brit and Colby! This was Chance’s very first wedding!
Day 13: Return to NYC
Final Notes & Pet Parent Travel Tips
Bucket List Note: Vermont fall foliage is a once-in-a-lifetime experience—add it to your must-see list
- Keep drives under 4 hours to prevent stress for your pup
- All Accommodations: Dog-friendly Airbnbs > chain hotels = all includes a kitchenette for Homemade meals for Chance and humans.
- Cooking in the hotels – helped save $$$ and it’s a lot healthier!
- Support local: Markets, cafes, breweries
- Bring eco gear: Reusable water bottles, collapsible bowls, compostable poop bags, wool blankets, cooking at “home” and booking Eco tourism for accomodations.
- Practice “Leave No Trace” whenever outdoors.
Vermont during peak foliage is expensive. Early planning and detours like Saratoga/Troy can save money and stress.
Finding pet-friendly accommodations in the Northeast Kingdom, peak Fall foliage weekend was very tough—and expensive! Clean, modern, conveniently located options ranged from $500 for a 2-star hotel to $2,000 for a 4-star. Airbnb options weren’t much better: a shared space might list for $300, but with additional pet and cleaning fees, it jumped to $800—often for less-than-ideal accommodations. Traveling with a dog really limits choices in this region during peak Fall Foliage season.
Note: This trip took place in 2022, and some pet policies may have changed since then. Be sure to check ahead and confirm current rules before you go.
Traveling with your dog isn’t just a getaway—it’s a chance to slow down, explore intentionally, and experience the world at your pup’s pace. On this roadtrip, we discovered that Vermont’s scenic trails, the Adirondacks’ peaceful hikes, and New York’s charming small towns are unforgettable when you travel slow, stick to dog-friendly routes, and prioritize your dog’s comfort.
Slow travel with dogs isn’t just a style of travel—it’s our ethos. By exploring at a dog’s pace, keeping routines, and choosing pet-friendly destinations, every walk, café stop, and scenic lookout becomes a moment to savor. Whether you’re planning a weekend dog-friendly trip, a cross-country adventure, or even international travel with your dog, embracing slow travel makes your journey more joyful, less stressful, and far more memorable.
If you want dog-friendly travel tips, slow travel itineraries, and insider guides for NYC and beyond, this blog is your go-to resource for planning unforgettable adventures with your four-legged companion.
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