Discover the Best Way to See Vermont: Inn-to-Inn Walking
- Updated: 04/04/2024
- Janice
Welcome to the peaceful beauty of Vermont, where one of the best ways to experience a visit is through an inn-to-inn walking adventure. With miles of scenic hiking trails, Vermont offers an idyllic setting for outdoor enthusiasts and nature lovers.
Imagine looking out to rolling green vistas or standing amid vibrant fall foliage while meandering through quaint towns, indulging in local cuisine and craft brews, and staying at one hospitable inn after another. If it sounds appealing, it is—highly.
For an anniversary trip, my husband and I loved experiencing Vermont this way. The leisurely pace of our walking trip gave us time to deeply appreciate its verdant natural beauty and the unique appeal of each new Vermont town and inn.
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So, whether you are a seasoned hiker or new to walking vacations, know that Vermont offers trails suitable for all skill levels. From the rugged slopes of the Green Mountains to gentle valleys with pretty lakes, we are sure you will find more than one route you will love.
What is an Inn-to-Inn Walking Trip?
If you are a nature enthusiast who loves to hike and walk while traveling but does not want to carry heavy gear, an inn-to-inn hiking vacation might be the ideal fit for your travel style. These multi-day trekking trips offer the perfect slow-travel adventure.
They allow you to experience the beauty of nature without sacrificing comfort. You get to enjoy the pleasure of the outdoors with only a day pack and then the ease of full-service and hospitable lodging at the end of each day. Plus, depending on your trip type, you may also get the convenience of someone else transferring your heavy luggage from one inn to the next.
You can do these trips as self-guided or as part of a guided group tour. Learn more about the benefits of each in my companion article, “9 Inn-to-Inn Hiking Tour Companies You Will Love.”
In addition to being a great way to see Vermont, inn-to-inn walking vacations offer an excellent way to explore the world. For example, this style of travel, thanks to its vast networks of well-marked and maintained trails and a seemingly endless supply of charming full-service inns, has been well-loved in Europe for years.
About Vermont, 3 Iconic Trails & How to Find More
For those not familiar, Vermont is a very rural state. More than 50% of its roads are unpaved, though well-graded. Its self-sufficient population hovers slightly above 600,000. Burlington is its largest city, with a population of under 50,000.
Vermont is known for its rolling green mountains, picturesque small towns, artisanal and locally sourced foods, and rich literary history.
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Though, Vermont was not always so green. Nearly 100 years ago, only 20% of Vermont forests remained after years of agricultural clearing and logging. Today, after a century of dedicated restoration, trees cover nearly 80% of the state. Learn more about the forest history in Vermont here.
So outdoor enthusiasts—rejoice! Vermont offers countless forested hiking trails that appeal to all skill levels and interests. See three of the most iconic routes below.
1. Long Trail
Stretching 273 miles along the spine of the Green Mountains, this trail takes hikers through remote wilderness areas, past breathtaking vistas, and to the summits of Vermont’s highest peaks.
2. The Appalachian Trail
While vast stretches of the Appalachian Trail pass through other states, a small portion winds through southern Vermont. This section offers a taste of the iconic beauty of the trail, with views, tranquil forests, and wildlife.
3. The Cross Vermont Trail
The Cross Vermont Trail is a developing multi-use trail that will eventually span the state from Lake Champlain to the Connecticut River. Several sections are open for walking, biking, and horseback riding, winding through forests, farmland, and small towns.
How to Find More Vermont Hiking Trails
In addition to these recognized trails, discover many other wonderful and lesser-known day hikes ranging from easy to challenging. See our sample itinerary below for the trails we hiked on our six-day Vermont walking trip.
To discover more hiking routes that best fit your skill and interests, use a resource like AllTrails, which features user-reviewed trails paired with essential logistics such as trail length, elevation gains, difficulty, route maps, and trailhead location.
When using AllTrails, search for trails throughout Vermont. Or focus on smaller geographic areas by searching for the name of a Vermont town where you plan to stay to find nearby hikes.
Then consider purchasing an AllTrails+ membership, which gives you download access to hiking maps. These offline maps allow you to GPS-track your walking progress when there is low or non-existent cell coverage, a great deterrent against getting lost.
A Sample Itinerary: A 6-Day Vermont Inn-to-Inn Walking Trip
To give you a glimpse of what an inn-to-inn walking trip in Vermont could look like, I share the itinerary from our six-day July Vermont inn-to-inn hiking getaway below.
Since I did not know Vermont or its hiking trails well, I relied on local expertise and booked our trip with the Vermont-based Inn to Inn Hiking company.
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Day 1: Arrive & drive to lodging in Bridgewater, Vermont
Day 2: Hike Killington Peak & stay at Mountain Top Resort
Day 3: Hike the Long Trail to Gillespie Peak & stay at Blueberry Hill Inn
Day 5: Hike the Mt. Moosalamoo Trail & stay at Swift House Inn
Day 6: Visit Shelburne Farms, explore Burlington, & return home
The above six-day Vermont itinerary serves as an example of what is possible on an inn-to-inn walking trip. Get the details for each day in the sections below.
Day 1: Arrive & Stay in Bridgewater, Vermont
On the first day of our Vermont trip, we arrived midday at the compact Burlington International Airport on a direct flight from our hometown of Chicago. After landing, we rented a car and drove just under two hours south to the small town of Bridgewater for our first night of lodging.
Upon arriving at the since-closed and former hiker favorite, October Country Inn, in Bridgewater, and a 15-minute drive from the pretty town of Woodstock, Vermont, we checked into our second-story and light-filled double room.
Once settled, we went back downstairs to grab a celebratory drink to enjoy on Adirondack chairs in the backyard, soaking up the late afternoon sun and toasting the start of our vacation. For dinner, we joined two other couples staying at the inn for a relaxed family-style dinner prepared by the inn owners and included in the price of our trip.
Since October Country Inn has sold and closed, consider staying at The Jackson House Inn or The Woodstocker B&B, two excellent alternatives in nearby Woodstock. Or, instead, book a second night at the Mountain Top Resort, our inn for day two.
Day 2: Hike Killington Peak & Stay at Mountain Top Resort
After a hearty breakfast, we picked up our prepared sack lunches and drove 30 minutes to tackle Killington Peak via Bucklin Trail, a 7.2-mile out-and-back trail with an elevation gain of 2,400 feet.
Parking our car at the trailhead, we enjoyed the first two miles of its gentle incline. After which, this shady and wooded trail progressively steepens, making for a challenging workout, ending with a fun scramble toward the summit.
On a clear day, like the one we were lucky to have, you can expect 360-degree views of Vermont’s Green Mountains from the Killington Peak summit—also an excellent place for a rest and picnic.
For a break on the way down, we stopped at the trail detour to pretty Irene Falls along Brewers Brook for a snack, a rest, and a chance to soak our tired feet before returning to our car and on to our next inn.
Alternative hikes to the Killington Peak summit include any of these listed on AllTrails, which range from easy to challenging in the Killington area.
Once back in our car, we drove another 30 minutes north to the lovely Mountain Top Resort. Sitting above the 750-acre pristine Chittenden Reservoir and tucked away in the heart of the Green Mountains, it was where we had a room booked for the evening.
After checking in, we headed to the pool and hot tub to soak our sore muscles and drink a beer in the setting sun. For dinner, we ate on-site at the hotel restaurant before collapsing in bed for an excellent night of sleep.
Read more about why this four-season resort is especially good for families, couples, and groups in the related article, “Why You Will Love Mountain Top Resort in Vermont.”
Day 3: Hike the Long Trail to Gillespie Peak & Stay at Blueberry Hill Inn
After hearing about Vermont’s famed nearly 300-mile Long Trail, we decided to hike a chunk of it, even just for a day. Using AllTrails to search trail options near Chittenden, we chose the out-and-back Gillespie Peak Via Long Trail, a 5.9-mile route.
Once we ate another generous breakfast on the sun-drenched Mountain Top Resort patio overlooking the reservoir, we grabbed our pre-prepared sack lunches, checked out, and drove 30 minutes to Brandon Gap and the trailhead to Gillespie Peak.
No slouches for uphill climbs, the hike to Gillespie Peak gained nearly 2,000 feet of elevation until it reached its partially obstructed summit. For the work, we found it to be not quite as rewarding as the panoramic expanse of Killington Peak the day before, but with fewer hikers on the trail, it felt like a peaceful walk in the woods paired with a thigh-burning and invigorating ascent.
Making our way back to the car by mid-afternoon, we drove a short 15 minutes to stay the next two evenings in the heart of the Moosalamoo National Recreation Area at Blueberry Hill Inn, my favorite inn—of many excellent ones—of the trip.
Family-owned and operated, this remote all-season inn is a historic gem. Built in 1813, the original Blueberry Hill Inn has since expanded to include 11 guest rooms and an Outdoor Center that maintains the miles of surrounding hiking and cross-country ski trails that begin on its doorstep.
Blueberry Hill Inn is the kind of place that former and now better-resourced round-the-world backpackers like us instantly recognize as truly relaxed, beloved, and tenderly cared for, imbued with the passion of its owners.
Our walk to our room through an interior greenhouse overflowing with plants and flowers alone was a lovely experience. And perhaps one of the prettiest entrances to a room we have had anywhere.
If you are fortunate enough to book a stay at the Blueberry Hill Inn in the summer or early fall, try to coordinate your arrival on a Pizza by the Pond night like we did.
This dinner is a weekly event hosted by the inn where guests and locals enjoy gourmet wood-fired pizzas and fresh-locally sourced salads topped with wild blueberry dressings outdoors while listening to live music.
Day 4: Loop Hike in the Moosalamoo National Recreation Area & Dinner in Middlebury
Waking at the Blueberry Hill Inn, we enjoyed a breakfast overflowing with good foods such as yogurt, berries, fresh granola, and a full plate of lemon zest blueberry pancakes, bacon, and eggs.
Planning to walk a series of connecting trails forming an approximately 7-mile loop that began behind the inn, we grabbed our pre-packed sack lunches and headed out.
Beginning our walk on the Hogback Loop Trail, we headed to the overlook, where we climbed the hill, picking and eating wild blueberries while enjoying the commanding view and keeping a lookout for bears and moose.
From here, and following the innkeeper’s recommendation, we took an offshoot trail to connect to the Halfdan Kunhle/Romance route. Along the way and heading to the Sucker Brook Trail to begin looping back to the inn, we saw an enormous moose on the path!
Keeping our distance to avoid scaring it and prompting a charge, we anxiously waited until it safely passed, keeping a sharp lookout for more unexpected friends along the trail.
Completing our loop on the Catamount Trail—a cross-country ski route in winter—we returned to the inn. Overall, we found it a lovely hike on well-maintained and signed paths with limited elevation gain on many sections. Plus, it was extraordinarily peaceful, given we saw fewer than five other hikers during our several-hour walk.
Once back, we dried off—it had been lightly raining for the last hour of our hike—and rested. Then, we drove a half hour along the curving roads north to nearby Middlebury, a charming New England town in the heart of the picturesque Champlain Valley. Often known best for being the home of Middlebury College, the town is prettily bisected by Otter Creek and its impressive cascade of Middlebury Falls.
Our innkeepers recommended dining at The Two Brothers Tavern, even making the reservation for us. Located in the heart of Middlebury on Main Street, the tavern is a popular eatery serving gastropub-style food, like the satisfying Korean fried chicken sandwich we ate, paired with one of several local craft brews on tap.
Day 5: Hike the Mt. Moosalamoo Trail & Stay at Swift House Inn in Middlebury
Beginning our day with another generous breakfast and seen off with our packed lunches, we headed out to hike the nearby Mount Moosalmoo trail, recommended by our innkeepers.
With an elevation gain of nearly 1,300 feet, this traditional 5.1-mile out-and-back trail has easy parking at the Moosalamoo campground lot. The route shares traffic with mountain bikers—though we saw none while hiking.
However, instead of returning along the same trail, we decided to make this hike into a loop, connecting to the Keeywadin Trail just past the Mount Moosalamoo summit.
In hindsight, I would have stuck walking back along the better-maintained and more trafficked Mount Mooslamoo trail. Because, once on the little-used Keeywadin Trail, we discovered the path in mid-July to be overgrown with ferns and often hard to find. Luckily, I had remembered to download an AllTrails contour map of the Mount Moosalamoo trail before our hike, which we referenced frequently to GPS-track our progress, ensuring we kept to the path and avoided off-route detours.
Once back at the campground, we picnicked at one of the open forested campsites, taking our time to soak up our final bit of forest before driving to Middlebury for our last night of the trip.
Alternative hikes to Mount Moosalamoo include any of these listed on AllTrails, which range from easy to challenging in the Moosalamoo National Recreation Area.
After arriving in Middlebury and checking into the Swift House Inn, a lovely 1800s colonial-style Vermont bed and breakfast on a sprawling and manicured property, we walked the short distance to town to explore and shop for souvenirs. Our favorite stop was The Stone Mill Public Market, a combo cafe and shop selling unique custom and locally-made wares and artisanal goods.
Is the Swift House Inn unavailable for your dates? Check out any of these other attractive Middlebury properties as alternatives.
For dinner, we took advantage of the inn’s sophisticated cocktail bar and a gourmet restaurant, Jessica’s, enjoying drinks and a meal of roast duck breast paired with farm-raised greens and a cheese plate.
Day 6: Visit Shelburne Farms, Explore Burlington & Return Home
On the final day of our trip, we woke to enjoy yet one more generous breakfast of an omelet and fresh fruit. At check-out, we picked up our packed lunch and drove north toward Burlington. Given our return flight did not depart until late afternoon, we gave ourselves time to stop en route at Shelburne Farms and then in downtown Burlington.
About a 40-minute drive from Middlebury, Shelburne Farms is an impressive working farm and educational non-profit estate dedicated to a sustainable future. In addition to exploring the grounds, visitors can stay and dine at its beautiful 24-room Gilded Age Shelburne Farms manor house overlooking Lake Champlain.
Although the manor house was closed the summer we visited, we walked around its formal gardens, enjoying the lake view, and picked a pretty spot to enjoy our packed lunches.
After lunch, we drove 20 minutes north to the heart of downtown Burlington. Parking on a side street, we headed to The Church Street Marketplace, Burlington’s main pedestrian shopping promenade. While strolling, we had just enough time to pick up some final Vermont souvenirs before returning to the airport and home after a fantastic Vermont visit.
How to Plan Your Vermont Inn-to-Inn Walking Trip: 6 Steps
To ensure a smooth and enjoyable Vermont inn-to-inn walking experience, here are six key planning steps to consider before a trip:
1. Decide if You Want to Book with a Tour Company (Guided or Self-Guided)
By booking your Vermont inn-to-inn walking trip with a tour company, you can expect to rely on their expertise and the convenience of having them manage the main elements of your trip, including lodging and several meals. Although you will pay more for a tour company inn-to-inn walking trip, you will get several benefits, such as established relationships with local inns and expert recommendations for the best routes, area experiences, and eateries.
However, by booking a trip on your own, you can expect to have more control over your itinerary and more flexibility in your choice of accommodation. To decide whether a self-guided or guided hiking trip is right for you—learn more about each here.
2. Decide Your Trip Duration
Determine how many days you want to spend on your walking trip. Be sure to factor in your preferred pace of travel, as well as whether you need rest days and would like to have time to explore the towns and attractions along the way.
3. Book Accommodations
If planning your trip independently, research and book accommodations at the inns along your chosen route. Vermont is known for its charming and cozy inns, so look for ones that offer the amenities and ambiance you desire. Consider factors such as location, room availability, and dining options.
4. Choose Your Routes
Once you know where you are staying, and depending on your trip, research the various hiking trails near each town you plan to stay in.
If planning your trip with a tour company, they might provide a fixed walking schedule to follow each day. Or share a selection of route options for different skill levels.
Further explore possible routes with a resource like AllTrails. And consider signing up for its AllTrails+ membership to download offline maps. Find trails that match your interests and skill level. Explore factors such as trail difficulty, length, and available amenities along the route.
5. Pack Appropriately
Pack essentials such as comfortable walking or hiking shoes, weather-appropriate clothing, a lightweight backpack, a water bottle, sunscreen, insect repellent, and a first aid kit. Also, consider bringing a paper map, compass, and any necessary navigation tools.
For more packing advice, see my recommended inn-to-inn packing essentials here. Add these items to my printable universal packing list.
6. Plan Your Meals
Research the dining options along your route and plan your meals accordingly. Some inns may offer on-site dining, while others may be located near local restaurants or markets, providing an excellent opportunity to explore new places. For popular eateries, make reservations to secure a spot.
8 Tips to Ensure a Successful Vermont Inn-to-Inn Walking Experience
To make the most of your inn-to-inn walking adventure in Vermont, consider the following tips:
1. Plan (Far) Ahead
Vermont is a small state with limited tourist capacity, particularly in the leaf-peeping season. If you plan to visit in the fall or summer, be sure to book far ahead, especially if you plan to book with a tour company with limited spots for each departure date. Even if you book your trip independently, planning will give you a prime pick of the best rooms at the best inns.
2. Be Prepared for No Cell Service
While driving or walking in rural areas of Vermont, know you might not have cell service. If you rely on cell phone mapping apps to navigate, download maps before you head out when you still have cell connectivity or access to Wi-Fi.
3. Prevent Against Bug Bites
Particularly in the summer, expect to encounter ticks and mosquitoes while hiking in Vermont. Wear hats and lightweight, long layers to protect against bites, and use bug repellant. After hikes, check for and remove ticks to avoid bites to help limit exposure to possible tick-related diseases.
4. Train & Prepare
If you are new to walking vacations or plan to tackle challenging trails, plan to train and prepare physically. Start by gradually increasing your walking distance and carrying a backpack with weight to build endurance.
5. Travel Light
It is important to pack light for easy lodging transfers and carry only the essentials to avoid unnecessary strain and discomfort. Choose lightweight and compact gear and opt for multi-purpose items.
6. Stay Hydrated & Fueled
On walking days—plan to drink plenty of water to stay hydrated. Carry snacks and energy bars to maintain energy levels during long hikes that might not have opportunities to refresh food and water.
7. Mind the Weather
The weather in Vermont can be unpredictable, so be prepared for changes in conditions. Check weather forecasts before each day’s walk and pack appropriate clothing for variable temperatures and weather patterns.
8. Take Breaks & Rest Days
Know your body. Take rest days and breaks as you need them. Many small Vermont towns offer lovely flat walks where you can explore galleries and independent shops. Or choose to stay put and enjoy the amenities at your Vermont inn, which often include comfortable lodging and beautiful outdoor spaces ideal for relaxing and reading a Vermont-themed book.
3 Vermont Tour Companies to Book Inn-to-Inn Hikes
The top two local tour providers for booking inn-to-inn walking trips in Vermont are Vermont Inn to Inn Walking and Inn to Inn. We booked our trip with Inn to Inn since they offered more flexible start dates and hiking options.
Additionally, Country Walkers, which offers walking trips throughout the US and abroad and was founded over 40 years ago in a barn in Vermont, has a Vermont Fall Foliage trip.
Discover more tour companies that offer international and local inn-to-inn walking trips in “9 Inn-to-Inn Hiking Tour Companies You Will Love.”
Takeaways
Whether you are a seasoned hiker or prefer more leisurely strolls, a Vermont inn-to-inn walking tour offers a lovely experience. This slow-travel way of exploring the Green Mountain State provides an excellent opportunity to see its natural beauty while enjoying the comfort and unique charm of hospitable inns. Expect to create cherished memories as you experience the best of Vermont, one step at a time.
Related Reading
For US New England travelers, check out these related articles for trip ideas and resources to help smooth your travel and get out the door with less hassle.
- The Best Books to Read Before a Vermont Trip
- Why You Will Love Mountain Top Resort in Vermont
- How to Make the Most of a Week in Acadia National Park
- 9 Inn-to-Inn Hiking Tour Companies You Will Love
- Pack Faster & Better With This Universal Printable Packing List
- 25 Expert Packing Tips to Help You Travel Better
- Pre-Trip: A Practical Checklist to Close the House & Pack
Additional Trip Planning Resources
To further help you with travel planning, I share my go-to resources for every trip below.
Google Flights. My first research stop for affordable flights for every trip. Learn why here.
Google Hotels. Use its “Where to stay” button to discover the best neighborhoods to base your visit.
Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.
Viator, Get Your Guide, & Airbnb Experiences. Quickly find and book highly-rated tours and activities on these sites.
Google Travel Things to Do & Google Maps. Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list.
AllTrails. Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.
Guide Along. 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour.
Insure My Trip. I never travel internationally without trip insurance. Learn why here. My preferred place to shop and compare policies is InsureMyTrip.com.
Plus, check out the 15 travel apps I use on trips, my preferred guidebooks, and my free customizable travel itinerary template, downloadable in four file formats.
About the author: Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog, Gather and Go Travel. Check out her bio, learn how she became a blogger, and discover how to work with her. Sign up for her monthly Discovery Newsletter to get her latest travel recommendations and how-to’s.
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Affiliate Disclosure: Some of the links on this page may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I only recommend products and companies I use. And the income goes to keeping the site community-supported and ads minimal.
Welcome to Gather and Go Travel, a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, an experienced traveler to over 50 countries and a travel writer, book lover, and blogger. Learn more about me, read our story, and how to work with me.
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