Walk the Nakasendo Trail

Ena, formerly known as Oi-juku, was once the 46th of the 69 post towns along the Nakasendo Way. In 1834, there were 41 guesthouses here, welcoming travellers making their way between Edo and Kyoto. Spend the day visiting the Hiroshige Museum, home to stunning woodblock prints that beautifully capture the essence of the Nakasendo by Utagawa Hiroshige and other artists. It’s the perfect start to your journey through Japan’s cultural and artistic past.

Begin your walk through small rural towns, passing rice paddies and gardens that give you an intimate glimpse of daily life in Japan. Arrive in Nakatsugawa, post town number 45, and explore its charming old town and traditional shops—perhaps sampling sweets or sake. If you're up for it, take a detour to the ruins of Naegi Castle for sweeping views (but be ready for a few extra kilometres!).

Ascent: 271 m | Descent: 241 m 

Today’s route is among the most iconic. Pass red torii gates and climb gradually to the famous village of Magome (post town 43), beautifully restored and full of traditional charm. Climb to Magome Pass (800 m), wander through forest trails and waterfalls, and arrive in picturesque Tsumago, with its long rows of preserved wooden houses—post town 42 of the original route. 

Ascent: 846 m | Descent: 745 m 

This is a day of deep immersion in nature. Follow a historic detour route over the Nenouetoge Pass—the Yogawa Route—once used during floods and landslides. Walk through cedar forests and mountain villages, tracing rivers and ridge lines. In autumn, the foliage here is truly spectacular. 

Ascent: 1044 m | Descent: 925 m

Today you can choose your own adventure. Take a break from the Nakasendo to explore the stunning Kaida Kogen Plateau, with scenic forest trails, waterfalls, and views from Jizo Pass (1,335 m). Walk as little or as much as you like—either 6 or 14 km, depending on your route. Prefer a rest? Explore Kiso-Fukushima and its quiet streets, or enjoy a short walk to Gongen Waterfall.

Take the train to Yabuhara and begin your final walk in the Kiso Valley. Cross the historic Torii Pass and descend into Narai, one of the most charming and beautifully preserved post towns on the route. After your walk, board a train to Nagano and continue by Shinkansen to Karuizawa.

Ascent: 507 m | Descent: 500 m

Your final walk takes you through the hills of Karuizawa and over the scenic Usui Pass. Enjoy mountain views from Miharashidai, visit tea houses or the Kumano Kotai Shrine, and descend through autumn forests into Yokokawa. The last stretch follows the old railway line—an atmospheric finish to your journey

Ascent: 701 m | Descent: 1253 m 

The Nakasendo Trail is for those who crave more than just a scenic walk — it’s for travellers ready to embrace a cultural journey across ancient paths, forested ridges, and small mountain villages where time seems to pause.

But don’t be fooled by the postcard beauty: this route comes with significant elevation and mountain terrain. It’s a moderately to challenging walk that requires preparation, especially if you're not used to hills or uneven paths. Some stages involve steep climbs, rocky sections, and long descents that can be tough on your legs if you're not conditioned.

If you live in a flat area, we strongly recommend training on stairs, treadmills with incline, or hill repeats to get used to the uphill effort. Elevation challenges a different set of muscles than flat walking — and is often where hikers struggle most. Squats, lunges, and core-strengthening exercises will help prepare your body and avoid injury.

The terrain is mountainous and uneven, so good balance and stability are essential. Think roots, rocks, forest trails — and the satisfaction that comes from mastering each one. Build up to it by increasing the technical difficulty of your training walks, and don’t overlook the value of good walking shoes with proper grip.

If you're looking for a cultural adventure on foot, love the idea of walking through misty cedar forests and past centuries-old inns, and are willing to train a bit to fully enjoy the journey — then yes, this walk is absolutely for you.

For our trips, we always choose accommodation with private rooms and private bathrooms. In rare cases, shared accommodations or shared bathrooms may be provided, so we recommend carefully checking the inclusions section to understand the type of accommodation included in the trip you are interested in.  

We place great importance on the choice of accommodations and select hotels with care and attention. We understand how essential it is to rest well after a day of walking. We always prefer cozy and characteristic establishments, preferably family-run, that fully embody the spirit of the place and offer hospitality with courtesy and comfort.  

Where, due to the nature of the route, accommodation options are limited, we choose the one that best aligns with our standards.

How to Arrive & Depart
Arrival – Getting to Nakatsugawa
Your journey begins in the historic town of Nakatsugawa, nestled in the Kiso Valley along the Nakasendo Trail. The most convenient way to reach it is via Nagoya, which is well connected by bullet train (Shinkansen) from both Tokyo and Osaka.

From Tokyo:
Take the Tokaido Line Shinkansen from Tokyo Station to Nagoya (approx. 1 hr 45 min). Tip: Sit on the right-hand side of the train for views of Mt. Fuji on clear days.
From Osaka:
Take a local train from Osaka to Shin-Osaka, then board the Tokaido Line Shinkansen to Nagoya (approx. 50 min).
From Nagoya to Nakatsugawa:
From Nagoya Station, take the JR Chuo Line (Rapid) to Nakatsugawa (approx. 1 hr 15 min). Both Rapid and Local services are available for the same fare.
If you are not using a JR Pass, buying a Non-Reserved Seat on the Shinkansen can save you money. Tickets can be purchased at the JR ticket window just before the Shinkansen gates.

Tip: Download the Japan Transit Planner or Japan Direct app – both are excellent tools for navigating Japan’s rail system, offering schedules, prices, and routes with or without a JR Pass.

Departure – After the Walk
From your final destination (often Tsumago or Magome), you can travel back to Nakatsugawa Station by local bus or taxi. From there, retrace your steps via Nagoya to Tokyo, Osaka, or your next destination in Japan.