Exploring Southern Oregon’s Vineyards Aboard the Jacksonville Wine Trolley

Southern Oregon’s wine country is a beloved destination for those who appreciate great wine, fascinating history, and memorable experiences. In the charming town of Jacksonville, you can explore celebrated vineyards and tasting rooms in a fun and convenient way—the Jacksonville Wine Trolley. This unique tour lets you sample local favorites like Awen Winecraft, Daisy Creek Vineyard, DANCIN Vineyards, Dos Mariposas Vineyards, Hummingbird Estate, and Rellik Winery. It also makes it easy to visit downtown tasting rooms, including Anchor Valley Wine, Somar Family Vineyards, Remotion Wine, and, of course, South Stage Cellars.

Whether you are an experienced wine lover or a curious traveler eager to explore local flavors, the Jacksonville Wine Trolley promises to excite your senses and spark your passion for wine.


A Brief History of the Jacksonville Wine Trolley

The Jacksonville Wine Trolley is more than just transportation. It is a celebration of local heritage and a nod to Jacksonville’s rich past. The idea came from a desire to link the charming downtown area with the sprawling vineyards outside town. By offering a safe and comfortable ride, the trolley helps you relax and enjoy your wine tasting day without worrying about driving afterward.

A review by Peggy Dover highlights the service as a game-changer for local tourism and commerce. Her account shows how the trolley meets the needs of wine lovers while also weaving in local history and the natural beauty of Southern Oregon. Whether you are a history buff or simply love a good glass of wine, the Jacksonville Wine Trolley has something memorable for everyone.


What to Expect on the Trolley

Imagine spending a lazy afternoon riding through beautiful landscapes while stopping at some of the best vineyards in the region. Here are some key points about the trolley experience:

  • Operating Hours:
    The service runs Friday through Sunday from 12:00 PM to 6:30 PM during the warmer months (May through October).

  • Pricing:
    For $25 (plus a small processing fee), you can secure an all-day pass that lets you enjoy a worry-free day of wine tasting.

  • Hub-and-Spoke Design:
    The tour starts and ends at the downtown Wine Trolley Stop on C Street. This stop is conveniently located near the Visitor Information Center and the local library. From here, you can also easily visit downtown tasting rooms, boutique shops, restaurants, and live music venues.

  • Timing:
    Each winery is visited approximately every 80 minutes, giving you plenty of time to sip and savor before the next stop.

  • Group Options:
    There are discounts for 2-day passes and for groups of five or more. This makes it a perfect option for celebrations, corporate outings, or a fun day out with friends.

If you’re ready for an immersive experience, check out the get tickets now page to reserve your spot.


A Winery-by-Winery Guide

The trolley stops at several unique wineries. Each one offers its own story, personality, and special wines. Let’s take a closer look:

Awen Winecraft

  • Overview:
    Awen Winecraft blends innovation with tradition. Known for its quality and creative approach, this winery serves a range of delicious wines.

  • Experience:
    Enjoy the friendly atmosphere and expert advice from the staff. It’s an ideal place to kick off your tasting journey.

Daisy Creek Vineyard

  • Overview:
    Nestled in a lush setting, Daisy Creek Vineyard is synonymous with excellent winemaking. The focus here is on pure, natural flavors.

  • Experience:
    With sustainable practices and a relaxed vibe, this vineyard offers a perfect spot for quiet conversation and savoring each sip.

DANCIN Vineyards

  • Overview:
    DANCIN Vineyards is known for its modern approach to winemaking. Its innovative techniques and dynamic wines make it a standout stop.

  • Experience:
    Engage with passionate vintners and enjoy a tasting that balances classic and experimental flavors.

Dos Mariposas Vineyards

  • Overview:
    This family-run vineyard celebrates tradition and craftsmanship. Dos Mariposas produces elegant wines that reflect the region’s rich soil and climate.

  • Experience:
    Enjoy a warm, familial welcome and immerse yourself in the story of perseverance and artisanal winemaking.

Hummingbird Estate

  • Overview:
    A small-scale, artisanal producer, Hummingbird Estate crafts wines that are true to their origins.

  • Experience:
    Feel the personal touch in every bottle and appreciate the community spirit behind each carefully curated selection.

Rellik Winery

  • Overview:
    Rellik Winery brings sophistication and bold flavors to the tour. It strikes a balance between innovation and classic winemaking techniques.

  • Experience:
    Known for its exceptional reds with complex layers of flavor, this winery often becomes the highlight for many visitors.


Downtown Delights: Tasting Rooms in Jacksonville

After exploring the vineyards, head to downtown Jacksonville where you can relax and enjoy more wine in a vibrant setting. The downtown area is just a short walk from the Wine Trolley Stop, making it easy to visit multiple tasting rooms:

Popular Downtown Tasting Rooms

  • Anchor Valley Wine & Somar Family Vineyards:
    These spots offer refined environments to enjoy a carefully curated selection of wines.

  • Remotion Wine:
    Renowned for its innovative blends, this tasting room provides a modern twist on classic wine culture.

  • South Stage Cellars:
    A local favorite, South Stage Cellars embodies the spirit of Southern Oregon’s wine culture. It not only serves a variety of wines that reflect the region’s unique terroir but also hosts regular events and special gatherings that bring the community together.

Pro Tip: Show your trolley wristband at these tasting rooms to receive a 10% discount—a thoughtful perk that makes the experience even sweeter.


Boosting Local Commerce and Community Spirit

The Jacksonville Wine Trolley is more than a fun ride—it is a vital part of the local economy. By linking vineyards and downtown tasting rooms, the trolley helps boost business for local retailers, restaurants, and lodging providers. This service strengthens community ties and supports the growth of Jacksonville’s wine culture.

Chamber President Brian Dunn highlights that every ride on the trolley builds a “vital connection” between rural vineyards and the downtown business community. As more visitors discover the charm of Jacksonville, services like the Wine Trolley set the standard for sustainable, community-focused tourism.

In my view, these innovative initiatives are exactly what small wine towns need. They preserve heritage while embracing modern trends—a win-win for everyone involved.


Insider Tips for a Great Trolley Adventure

Here are some tips to help you get the most out of your day on the Jacksonville Wine Trolley:

  • Plan Ahead:
    Check the schedule on the Jacksonville Wine Trolley page and plan your stops. Arriving a bit early at your first winery lets you settle in and enjoy the atmosphere.

  • Ride with a Group:
    Sharing the experience with friends, family, or colleagues makes it more fun and can help you save with group discounts.

  • Stay Hydrated and Snack Smart:
    Even though wine is the highlight, drinking water and enjoying light bites will keep you comfortable throughout the day.

  • Dress Comfortably:
    Wear layers and comfortable shoes since you will be both riding and walking between stops.

  • Engage with the Hosts:
    Ask questions and learn about the winemaking process. The staff at each winery is knowledgeable and friendly.

  • Take Advantage of Discounts:
    Your trolley wristband unlocks special discounts at downtown tasting rooms like South Stage Cellars—don’t forget to use it!

  • Capture the Moments:
    Bring your camera or smartphone to snap photos of the beautiful vineyards, historic buildings, and joyful moments along the way.


The Future of Wine Tourism in Jacksonville

The Jacksonville Wine Trolley is quickly becoming a cornerstone of Southern Oregon’s wine tourism. This innovative service connects sprawling vineyards with downtown tasting rooms, creating a network that benefits both local businesses and visitors. As more people learn about Jacksonville’s charm, the trolley service may expand its routes and even offer themed tours that dive deeper into the history and art of winemaking.

At South Stage Cellars, the spirit of innovation is also alive. Beyond offering an outstanding selection of wines, South Stage hosts events that celebrate local culture and community. Their events page and menu are a great resource for anyone who wants to experience the best of what Southern Oregon has to offer.

In many ways, the Jacksonville Wine Trolley captures the essence of Southern Oregon. It is a blend of history, modern innovation, and a strong community spirit. This service is more than just a ride—it’s an invitation to join a living, breathing community of wine enthusiasts.


Personal Reflections: Why I Love the Trolley Experience

After exploring many wine regions over the years, I can honestly say that the Jacksonville Wine Trolley is one of the most enriching experiences I’ve encountered. There is something truly special about being part of a journey that combines great wine, engaging conversations, and the beauty of the local landscape. Whether you are riding alone and making new friends or enjoying the day with a group, the trolley experience offers a unique way to connect with both people and place.

What I love most is how accessible it is. Wine tasting can sometimes feel exclusive, but the trolley makes it easy for everyone to join in the fun. The friendly vibe, thoughtful planning, and safe transportation allow you to relax, enjoy every moment, and truly appreciate the art of winemaking.


A Call to Experience the Best of Jacksonville Wine Country

If you’re reading this and feel that spark of curiosity, I encourage you to try the Jacksonville Wine Trolley for yourself. It is more than just a mode of transport—it is a gateway to exploring the heart and soul of Southern Oregon’s wine country. From the innovative techniques at Awen Winecraft to the rich traditions of Dos Mariposas Vineyards, every stop offers its own unique taste and story.

And when your journey brings you back to downtown, make sure to stop by South Stage Cellars. This is not only a place to enjoy exceptional wines but also a hub for community events, live music, and unforgettable gatherings. It is the perfect complement to your day of exploration.

Booking your ride is simple. Just visit the get tickets now page to secure your all-day pass. Then, sit back, relax, and get ready for a day full of delightful wine and engaging experiences.


Embracing the Journey, One Sip at a Time

The Jacksonville Wine Trolley embodies everything wonderful about Southern Oregon’s wine country. With each vineyard stop and downtown tasting room visit, you are not just sampling wines—you are experiencing history, community, and the passion behind every bottle.

For South Stage Cellars, hosting a part of this remarkable journey means more than serving wine. It is about celebrating tradition, fostering community, and paving the way for future generations of winemakers. Whether you are a local resident or a visitor from afar, the trolley experience is a gentle invitation to slow down, savor each moment, and enjoy the art of winemaking.

So, what are you waiting for? Plan your day, gather your friends, and step into an adventure that promises exceptional wines and unforgettable memories. Check out the get tickets now link, and don’t forget to visit South Stage Cellars to round off your day with a final toast.


Frequently Asked Questions (FAQ)

  1. What is the Jacksonville Wine Trolley?
    The Jacksonville Wine Trolley is a guided tour that takes you from downtown Jacksonville to several local wineries, offering a safe and convenient way to enjoy wine tastings without the worry of driving.

  2. What are the operating days and hours?
    The trolley runs from Friday through Sunday during the warmer months (May–October) from 12:00 PM to 6:30 PM, making it easy to plan your day around wine tasting and exploration.

  3. How much does a ticket cost, and are there any discounts?
    Tickets are priced at $25 (plus a small processing fee) for an all-day pass. Discounts are available for 2-day passes and for groups of five or more people.

  4. Which wineries are included in the tour?
    The trolley stops at several local favorites, including Awen Winecraft, Daisy Creek Vineyard, DANCIN Vineyards, Dos Mariposas Vineyards, Hummingbird Estate, and Rellik Winery. Plus, you can easily visit downtown tasting rooms such as Anchor Valley Wine, Somar Family Vineyards, Remotion Wine, and South Stage Cellars.

  5. How do I book my ride on the trolley?
    Booking is simple—just visit the get tickets now page to secure your spot and check out the latest schedule and pricing details.

Feel free to reach out if you have any more questions, and enjoy your journey through Southern Oregon’s wine country!