Road Trip

Richmond → West Windsor

Drive with dog breaks, settle in, simple dinner.

Driving directions ↗

Mount Ascutney + Windsor

Choose a light loop or a summit-area hike on Mount Ascutney, then stroll Windsor’s historic Main Street. The American Precision Museum and Cornish-Windsor Covered Bridge make specific stops; pick up coffee, sandwiches, and dinner provisions.

Light hike: Slot Trail · 1.2 mi loop ↗ · Mount Ascutney State Park ↗ · American Precision Museum ↗ · Cornish-Windsor Covered Bridge ↗

Brownsville Butcher & Pantry ↗

Burlington → Stowe → Moss Glen Falls

Dogs come along. Coffee and breakfast, Church Street and waterfront, market sandwiches to picnic by the lake, then a short waterfall walk. Pick up dinner ingredients for the Airbnb; bring a cooler.

Waterfront ↗ · Moss Glen Falls ↗ · Stowe ↗

August First ↗ · Poppy Café ↗

Killington area

Easy waterfall walk and mountain scenery. Breakfast burrito or deli sandwiches; shop local groceries on the way back.

Thundering Brook Falls ↗

Killington Deli ↗ · Killington Market ↗

Open Vermont day

Short town or park walks, coffee, slow afternoon, cook at the Airbnb. Leave this open for rain or a favorite spot worth revisiting.

Quechee Gorge ↗ · Windsor historic village ↗

Sugarbush Farm ↗ — Optional cheese and maple tasting near Woodstock; you’ll need to take turns inside with the dogs.

Dinner: Worthy Burger ↗ — Burgers, salmon sandwich, or black bean burger. Fries are cooked in beef tallow.

Dog Chapel → Québec

Must-do: Dog Mountain in St. Johnsbury around chapel opening, then continue north to Québec. Reconfirm hours before departure.

Dog Chapel ↗ · Directions via Dog Chapel ↗

Jacques-Cartier National Park

Try La Tourbière for an easy dog-friendly walk: a 2.9 km loop, about an hour, starting at km 3. Dogs are allowed on this trail May–November, subject to trail conditions. Pack lunch; cook dinner back at the stay.

La Tourbière trailhead parking · km 3 ↗ · Official trail details ↗ · Dog access map and rules ↗

Old Québec + Montmorency Falls

Historic streets, coffee and casual takeaway; waterfall viewpoints afterward. Could be a dogs-at-Airbnb city outing if preferred.

Old Québec ↗ · Petit-Champlain ↗ · Montmorency Falls ↗

Lunch: Le Chic Shack ↗ — Near Château Frontenac for poutine or burgers; veggie burger and vegan poutine options for the pescatarian. Or Quai 1635 ↗ in Cap-Rouge for a riverside lobster roll; check fall hours, since the restaurant is seasonal.

Charlevoix or Île d’Orléans

Pick a longer scenic drive to Baie-Saint-Paul or an easier island food-and-villages loop; market stop for dinner supplies.

Baie-Saint-Paul ↗ · Île d’Orléans ↗

Québec → Montréal

Easy driving day with optional waterfront/lunch break in Trois-Rivières. Check in at Longueuil.

Trois-Rivières ↗ · Directions via Trois-Rivières ↗

Mount Royal + Plateau / Mile End

Park walk, neighborhood wandering, specialty coffee and takeaway. Dogs can join the outdoor parts; choose what feels manageable.

Mount Royal ↗ · Plateau ↗ · Mile End ↗

St-Viateur Bagel ↗ — Bagel stop; cream cheese or smoked salmon for the pescatarian.

Old Montréal

Historic streets and Old Port. Bakery or sandwich stop; look for a lobster roll on this leg if there’s a good option.

Old Montréal ↗ · Old Port ↗

Olive et Gourmando ↗

Montréal → Saugerties

Cross the border, take dog breaks, check in after 3 PM. Easy takeout dinner.

Driving directions ↗

Catskills + Woodstock, NY

Overlook Mountain or Kaaterskill Falls, then town wandering and a casual lunch. Saugerties coffee/breakfast option before heading out.

Overlook Mountain ↗ · Kaaterskill Falls ↗ · Woodstock ↗

Breakfast: Olsen & Company ↗ · Dinner: Miss Lucy’s Kitchen ↗ — Near the stay, with fish and chips or a salmon salad option.

Saugerties → Richmond

Drive home. Optional Walkway Over the Hudson for a scenic dog stretch if weather and timing allow.

Walkway Over the Hudson ↗ · Driving directions ↗