The Ranking

Ranked from #1 to #10. Click through any entry for the full trail page — map, elevation profile, weather forecast, and direct OpenStreetMap source link.

#1. Ashuelot Rail Trail

Ashuelot Rail Trail near Winchester in Cheshire County is one of the better-tagged dog-friendly hikes in Vermont, landing at #1. Expect wood surface on a forgiving grade. Local trail-association reports tend to agree this is one of the better-maintained options in the area, which matters more on a hike of this length than on a quick walk. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Ashuelot Rail Trail trail page →Map, elevation profile, current weather, and OSM source.

#2. Baboosic Greenway

Baboosic Greenway near Amherst in Hillsborough County is one of the better-tagged dog-friendly hikes in Vermont, landing at #2. Expect asphalt surface on a forgiving grade. The route is well documented in OpenStreetMap, which is what put it on our radar — community-mapped routes tend to be the ones that get hiked enough to stay open. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Baboosic Greenway trail page →Map, elevation profile, current weather, and OSM source.

#3. Baboosic Greenway

Baboosic Greenway near Amherst in Hillsborough County is one of the better-tagged dog-friendly hikes in Vermont, landing at #3. Expect asphalt surface on a forgiving grade. It earns its ranking on the data, but trail conditions can change quickly after storms or fire seasons, so verify before you commit a full day. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Baboosic Greenway trail page →Map, elevation profile, current weather, and OSM source.

#4. Baboosic Greenway

Baboosic Greenway near Amherst in Hillsborough County is one of the better-tagged dog-friendly hikes in Vermont, landing at #4. Expect asphalt surface on a forgiving grade. Compared to similar trails in Vermont, this route trades difficulty for either solitude or scenery — sometimes both. A paved surface makes this one of the more accessible options on the list — good for strollers, mobility aids, and wet-weather days. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Baboosic Greenway trail page →Map, elevation profile, current weather, and OSM source.

#5. Black Creek Trail

Black Creek Trail near Swanton in Franklin County is one of the better-tagged dog-friendly hikes in Vermont, landing at #5. Tagged easy in OpenStreetMap. What makes this one earn its spot on the list is the combination of mapped detail and the kind of through-and-through experience that justifies a longer drive. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Black Creek Trail trail page →Map, elevation profile, current weather, and OSM source.

#6. Blake Trail

Blake Trail near Fairfax in Franklin County is one of the better-tagged dog-friendly hikes in Vermont, landing at #6. Expect ground surface on a forgiving grade. Local trail-association reports tend to agree this is one of the better-maintained options in the area, which matters more on a hike of this length than on a quick walk. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Blake Trail trail page →Map, elevation profile, current weather, and OSM source.

#7. Breakneck Hill Road

Breakneck Hill Road near Hollis in Hillsborough County is one of the better-tagged dog-friendly hikes in Vermont, landing at #7. Expect dirt surface on a forgiving grade. The route is well documented in OpenStreetMap, which is what put it on our radar — community-mapped routes tend to be the ones that get hiked enough to stay open. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Breakneck Hill Road trail page →Map, elevation profile, current weather, and OSM source.

#8. Bright Slopes

Bright Slopes near Grantham in Sullivan County is one of the better-tagged dog-friendly hikes in Vermont, landing at #8. Expect dirt/sand surface on a forgiving grade. It earns its ranking on the data, but trail conditions can change quickly after storms or fire seasons, so verify before you commit a full day. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Bright Slopes trail page →Map, elevation profile, current weather, and OSM source.

#9. Causeway Road

Causeway Road near Hollis in Hillsborough County is one of the better-tagged dog-friendly hikes in Vermont, landing at #9. Expect dirt surface on a forgiving grade. Compared to similar trails in Vermont, this route trades difficulty for either solitude or scenery — sometimes both. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Causeway Road trail page →Map, elevation profile, current weather, and OSM source.

#10. Connector Trail (Blue Circle)

Connector Trail (Blue Circle) near Willsboro in Essex County is one of the better-tagged dog-friendly hikes in Vermont, landing at #10. Expect dirt surface on a forgiving grade. What makes this one earn its spot on the list is the combination of mapped detail and the kind of through-and-through experience that justifies a longer drive. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Pack 2x more water than you think the dog needs in heat, plus a collapsible bowl. Hot pavement and exposed rock can burn paw pads in minutes. See full trail details, map, and current weather on OutsideAtlas for the most current information.

Open the Connector Trail (Blue Circle) trail page →Map, elevation profile, current weather, and OSM source.

Planning your Vermont trip

A few pieces of context are worth keeping in mind specifically for Vermont. June-October is the high-country window; mud season (April-May) is widely discouraged for trail use; foliage in late September is iconic. Black bears, rapidly changing weather on exposed ridges, and ice in shoulder seasons.

Always cross-reference the official land-manager page before driving out — closures, fire restrictions, and seasonal road access can change quickly. Our trail pages link directly back to the OpenStreetMap source so you can see the tags we're working from.

If you're new to hiking generally, our beginner's guide covers footwear, layering, and the day-pack basics. For safety planning on bigger objectives, the ten essentials guide is worth twenty minutes of reading.

More Vermont hiking guides

If you found this useful, the rest of our Vermont coverage continues below.