October Road Trip

October 7–21, 2026

Route & stays

Wed, Oct 7

Richmond, Virginia · depart early morning

Oct 7–12

West Windsor, Vermont · 5 nights

Oct 12–16

Sainte-Brigitte-de-Laval, Québec · 4 nights

Oct 16–19

Longueuil / Montréal, Québec · 3 nights

Oct 19–21

Saugerties, New York · 2 nights

Wed, Oct 21

Richmond, Virginia · arrive late evening

Day by day · working draft

Wed 7 🚗

Richmond → West Windsor

Drive with dog breaks, settle in, simple dinner.

Route ↗

Driving day

Thu 8

Mount Ascutney + Windsor

Short summit-area hike or a longer trail, depending on weather. Grab coffee and sandwiches; browse local provisions for a cooked dinner.

Mount Ascutney ↗ · Windsor ↗ · Brownsville Butcher & Pantry ↗

Proposed

Fri 9

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.

August First ↗ · Poppy Café ↗ · Waterfront ↗ · Moss Glen Falls ↗ · Stowe ↗

Proposed · full dog day

Sat 10

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 ↗

Option

Sun 11

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 ↗

Flexible

Mon 12 🚗

Dog Chapel → Québec

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

Dog Chapel ↗ · Québec stay ↗

Driving day · fixed stop

Tue 13

Jacques-Cartier National Park

Choose a dog-permitted valley or forest trail for a waterfall/river-and-mountain day. Pack lunch; cook dinner back at the stay.

Park ↗ · Les Coulées ↗

Option

Wed 14

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 ↗

Option

Thu 15

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 ↗

Flexible

Fri 16 🚗

Québec → Montréal

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

Trois-Rivières ↗ · Longueuil ↗

Driving day

Sat 17

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 ↗

Option

Sun 18

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 ↗

Option

Mon 19 🚗

Montréal → Saugerties

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

Route ↗ · Saugerties ↗

Driving day

Tue 20

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 ↗ · Olsen & Company ↗

Flexible

Wed 21 🚗

Saugerties → Richmond

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

Walkway Over the Hudson ↗ · Route ↗

Driving day

Hit list

Lobster rolls

Packing list

Rain jacket, warm layers, hiking shoes, gloves, and a beanie.
Swimsuit / trunks, just in case.
Cooler, ice packs, picnic blanket, travel mugs, and daypack.
Dog crates, towels, water bowl, leashes, food, medications, and dog camera.
Passports and all required paperwork for the dogs to enter Canada and return to the U.S.

Loading shared checklist…

Plans are provisional except Airbnb dates and the Dog Chapel stop. Adjust outdoor days as the weather forecast becomes reliable.