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Self-Guided Walking Tours
Explore the beauty of Southern Vermont at your own pace
A Walking Vacation,
Without the Logistics
Spend four days walking through southern Vermont at your own pace, following self-guided routes between four distinct inns. Each morning, head out with just your daypack while we transport your luggage ahead to the next inn.
Along the way, you’ll pass through small villages, quiet country roads, wooded trails and classic Vermont scenery — with dinner waiting when you arrive and breakfast the next morning.
Four Inns, Four Distinctive Stays
One of the best parts of the Walking Tour is that no two nights feel exactly alike. Each of our four independently owned Vermont inns has its own personality, setting and style — from historic village inns to a renovated motor lodge.
Your four-night package includes lodging, dinner and breakfast at each stop, giving you a chance to experience each inn’s own style of hospitality.
Here’s what the Vermont Inn to Inn Walking Tour Package Rates include:
Five days and four nights — each night at a different Vermont inn
private guest room & private bathroom at each inn
Full gourmet country breakfast each morning
Afternoon refreshments at each inn
Three Course Dinner each night
Trail snacks for the day’s walk
Daily luggage transfers
Detailed trail maps and route notes
Route Guidance
All taxes
Fall may be Vermont’s most famous season, with crisp air and brilliant foliage — but each season offers its own distinct walking experience.
Spring brings rushing streams, wildflowers and quieter roads, while summer offers long days, lush green mountains and warm-weather walking.
Fall brings cooler temperatures and the classic New England scenery Vermont is known for.
Explore each season to find the timing that feels right for your trip.
Walking Vermont
by Season
Peak Demand Fall
Late September–mid October
Our most requested fall dates, with crisp days and classic Vermont scenery.*
*Foliage varies year-to-year and we cannot guarantee timing or fall color.
Pricing
$3,598
Single occupancy $3,598 per person
$3,798
Per couple / double occupancy $1,899 per person
$5,697
Triple occupancy in the same room $1,899 per person
All rates shown are the total price for the complete four-night Walking Tour package. Per-person pricing is included above to make comparing occupancy options easier. Fall foliage departures are traditionally our most popular and often fill quickly, so we encourage booking early for your preferred dates. Please visit our Book Now page for current dates and availability.
Seasonal Temperatures at a Glance in Southern Vermont
Weather varies year to year, but overall the Green Mountains remain one of the cooler and more comfortable regions for walking tours from late spring through early fall.
May
Highs in the mid-60s to low 70s
June
Highs in the low to mid-70s
July
Highs in the mid-70s to low 80s
September
Highs in the mid-60s to low 70s
August
Mid-70s to around 80
October
Highs in the 50s, cooler mornings and evenings
Cancellation / Postponement, Date Changes
We understand that some circumstances may arise causing a need to cancel, so we want to be upfront and clear regarding our policies. To secure your reservation, we require a deposit of 50% of the cost of your tour. Once this deposit is paid, half of your deposit is immediately non-refundable. One month prior to your tour start date, the remaining 50% of your tour price is due. Once this second payment is made, all monies paid are fully non-refundable.
Cancellations never happen for a happy reason. With that in mind it may be wise to protect your vacation investment with trip insurance. Examples may include your credit card company, specialty insurance company’s such as Allianz Travel ( www.allianztravelinsurance.com ), and others.
Vermont Inn to Inn Walking Tours does not absorb the cost of cancellations, postponements or date changes; indeed, the policy is strictly enforced.
If a cancellation is made more than 30 days in advance of your tour start date, 50% of the deposit will be forfeited and 50% refunded. If a cancellation is made within 30 days of the tour start date, there are absolutely no refunds or credits of any portion of the tour payments.
Postponements and date changes are largely regarded the same as cancellations, however if a postponement is made more than 30 days in advance of the start date, we can reduce the forfeited fee to 25% of the deposit, and 75% of the deposit will be applied to the future reservation.
Rates apply to adults and children age 15 and older.
Children under 15 cannot be accommodated on tours.
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Explore Southern Vermont
Extend your trip and explore more of what Southern Vermont has to offer!
Outdoors & Waterfalls
Southern Vermont’s forests, rivers, and mountain trails invite you outside in every season. Discover nearby waterfalls, swimming holes, and scenic places to explore at your own pace.
Arts & Theater
Southern Vermont’s creative spirit comes alive in intimate theaters, galleries, and artisan studios. Enjoy a performance, browse local artwork, or meet the makers behind it.
Farms & Food
Discover farm stands, farmers markets, maple producers, and locally made treats throughout the region. Taste what’s in season and meet the people who grow and create it.
Shopping & Antiques
Browse independent shops, antique centers, bookstores, and galleries filled with one-of-a-kind finds. Take home something with a little Vermont history and character.
Historic Villages
Wander through postcard-worthy village centers lined with historic homes, churches, and covered bridges. Slow down and explore the distinctive character of each community.
Museums & Historic Sites
Step into Vermont’s past through presidential homes, working farms, and places that helped shape American history and industry.
Seasonal Events
From summer concerts and country fairs to fall festivals and holiday traditions, there is always something happening. See what’s on during your stay and experience Southern Vermont in season.
Covered Bridges
Discover historic covered bridges tucked among river valleys, village roads, and scenic countryside. Each one offers a glimpse of Vermont’s enduring craftsmanship and character.
Worth the Drive
Have an extra day to explore? These iconic Vermont destinations are farther from our inns, but well worth the journey.