The Best Inn-To-Inn Hikes In America

Channel your inner European.

By
Published July 24, 2026
Golden Gate Bridge illuminated against a colorful twilight sky overlooking calm water and coastal vegetation
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In the United States, hiking often connotes rugged, unfriendly conditions, only for hardcore outdoorsy types. But this isn’t necessarily true. Inn-to-inn hiking can promise savory meals, hot showers, and cozy beds at the end of a peaceful, unhurried day’s walk in nature. Personally, this is my preferred mode of hiking: steps, beautiful scenery, and cozy lodgings at the end of each day.

Unlike in Europe — where it's commonplace — in the U.S., inn-to-inn hiking is less available and thus less known. But it shouldn’t be. Curious? The following inn-to-inn hiking routes will help those who are interested but unsure where to begin.

California: San Francisco to the Wine Country

Forest pathway surrounded by massive redwood trees and lush greenery, with a distant visitor walking along the trail
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Let’s begin in California with raised wine glasses to toast an adventure that pairs walking with wine. Wine Country Trekking offers a 10-day dreamy hiking excursion that begins in San Francisco and concludes in the vineyards of Sonoma.

Included in National Geographic Traveler’s “50 Tours of a Lifetime,” the self-guided walking tour kicks off downtown at Fisherman’s Wharf for a time of sightseeing — no hiking, just an opportunity to arrive, meet your friends, and get your bearings. Day two starts the walking adventure, which includes crossing the Golden Gate Bridge, visiting Sausalito, Muir Woods National Monument, and Tomales Bay.

Though slated for 10 days, there are actually just six days of hiking with one full “off day” in Tomales Bay, where you have the option to kayak. Expect to walk 8 to 12 miles a day, with the final day walking from vineyard to vineyard to taste the best of Sonoma wines. After a day of stunning redwoods, rolling country, and ocean views, end with a comfy stay at an English Tudor-style inn, waterfront property, or luxury hotel with a spa.

The dining experiences are as outstanding as the vistas, with a classic, personality-rich village pub to a restaurant serving West Marin’s best farm-to-table produce and fish. The tour covers full-scale breakfasts and premium wine tastings but doesn’t include lunch or dinner. Your complete itinerary, trail notes, and maps will also include information on where to buy fresh, daily picnic lunches for the trek.

Vermont: Vermont Inn-to-Inn Walking Tours

Panoramic mountain valley covered in colorful autumn trees with shades of red, orange, yellow, and green beneath a bright blue sky
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This picture-book New England country walking tour is a 4-day, 42.5-mile self-guided hike. It allows you to go at your own pace with your friends, aided by trail maps. It’s great for those who are moderate hikers (ranging from 7 to 13 miles per day), love their independence, but appreciate behind-the-scenes support to book stays, handle luggage, and receive in-depth trail insights. Essentially, all you have to do is relax, have fun, and soak in Vermont’s famed pastoral landscape.

Remember that Vermont is a diva when it comes to autumn colors, so if you’re catching the area’s legendary foliage, aim for September or October when the colors peak. The inn-to-inn walk is along mostly quiet wooded dirt roads winding through the Green Mountains — so be prepared for hilly terrain. It’s circular: park at the first inn, and arrive 4 days later to pick up your car. Bags are automatically transferred from inn to inn so that you can leave each morning with a small backpack just with the essentials.

At the end of each day, a classic BnB or charming inn is waiting with food, drink, and a comfortable room. Some stays are in villages with shops and pubs, while others are in the country. Three-course home-cooked dinners will help recharge your batteries. Breakfast and healthy snacks for the road set you up for a strong day.

Oregon: 4-Day WIKING (Wine Hike) Trip

Colorful pink and red wildflowers bloom along a coastal hillside overlooking blue water and a large arched bridge
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Turn off your phone and dip your toe in an off-the-grid wilderness adventure featuring Oregon’s gorgeous Rogue River. But don’t panic — though the 4-day, 4-night canyon trek is exotic and ensures digital detox, you’ll have professional guides with you the entire time. It’s tremendously nature-rich as well as being wine-forward, thanks to the meticulous planning by Morrison’s Rogue Wilderness Adventures and Lodge.

Covering 40 miles in 4 days, the path follows the scenic Rogue River, and rafting is always an option to rest tired feet. With a daypack for water, layers, and sunscreen, expect to cover 7 to 15 miles per day. Trail guides will pilot rafts to transport luggage, serve midday riverside buffet lunches, and provide ready support as needed.

Your starting point is Morrison’s Rogue River Lodge with cozy rooms, a gourmet menu, and a farmer’s breakfast. Over the following days, you’ll stay at family-owned pristine lodges powered by generators — ensconced in nature and refreshingly offbeat. Black Bar Lodge has log cabins and is remote, accessible only from the trail and river. Marial Lodge is known for its family-oriented hospitality and home-cooked meals. And the final overnight is with Paradise Lodge, a popular, large rustic property flanked by steep canyon walls. Each evening, anticipate delicious meals and some tippling with local winemaker Liz Wan, who conducts educational wine tastings.

Have YOU ever gone on an inn-to-inn walking vacation? Would you like to? Let us know in the comments below.

Kathryn Streeter is a freelance writer living in Washington, D.C. whose work has appeared in USA Today, The Washington Post, Islands, The Week and elsewhere. Learn more at KathrynStreeter.com.