319 Meeker St. Galena, IL 61036



Massbach Ridge Winery

See Why You Should Plan a Galena Winery Tour This Spring

A Great Galena Winery Tour for 2020Have you taken a Galena Winery Tour yet? This spring might just be the perfect opportunity!  If you’ve never visited Galena before, it might come as a surprise to learn that the Galena area is actually home to some of the top award-winning wineries in the state of Illinois. There are a number of wineries in the area, each of which offers something unique and is worth visiting.

There is, of course, plenty to do in downtown Galena to keep you busy during a weekend getaway, but we’d be remiss not to mention all of the great things to do in the surrounding area!  One of our favorites is taking Galena Winery Tours. These tours are the perfect way not just to taste the delicious wines grown and produced here, but also to learn more about what makes these wines so appealing and see the area’s beautiful countryside. Don’t miss this opportunity.  Book your room at our Galena Bed and Breakfast Today!

2 Great Galena Winery Tours to Take This Spring

If you’re at all a wine lover, Galena really should be on your radar. This quaint, historic little town is home to 6 great wineries and hosts several wine events throughout the year. These events, including Corkless in Galena and Wine Lovers Weekends, have huge draws from the greater Chicago area and across Illinois. Lodging for events like these often book up far in advance, as they provide some of the best wine tasting opportunities in the Midwest.

A Great Galena Winery Tour for 2020

If you can’t make it to one of those great events this year, it’s not a problem. Galena Winery tours can be enjoyed at any time throughout the remainder of the year! Here are 2 great companies that offer winery tours in Galena.

  1. Countryside Tours offers a number of winery tours in the Galena area. Each tour is different but includes 4 hours of fun and 3 wine-tasting stops along the way. Their Wine Tasting Tour includes 3 stops at one of Galena’s 6 wineries and includes up to 9 delicious tastings. They also offer a Hop Tour, which includes a broader range of tastings. The tour includes a stop at 1 vineyard and 1 or 2 stops at what they describe as “very unique drinking establishment from the 1850s and/or a distillery.” All tours depart from their set location in downtown Galena, which is very walkable from our Inn.
  2. Galena Wine Tours offers you the gateway to a fun-filled day in the vineyards around Galena. Galena Wine Tours will pick you up directly from the Jail Hill Inn before heading out on your chosen adventure. They offer 3 different Galena Winery Tours, which include the Blackhawk Wine Tour, their Winery/Council Hill Tour, and the My Favorite Places Galena Tour. Each is different, but all offer great wine tasting experiences and plenty of fun and scenic adventure along the way.

Galena Wineries to Visit

If you’d rather venture out and discover the many Wineries around Galena on your own, here are the 6 places you’ll want to consider!

  • Galena Cellars, probably the most recognized Galena Winery, also offers their own public Vineyard tours. They offer wine tastings at their downtown Galena location and their winery, and also host a number of events throughout the year.
  • Massbach Ridge Winery also offers tours of their vineyard, and they have a tasting room both at the winery and in downtown Galena.
  • Rocky Waters Winery has a fully-stocked wine room, and they offer both tastings and tours onsight.
  • A short ways away in Hanover is Fergedaboudit Winery, and they offer an onsight tasting room.
  • In Dubuque, you’ll find Stone Cliff Winery, which has a beautiful tasting room and a café. It’s the perfect place to grab lunch and enjoy a relaxing afternoon. They also have outdoor seating for those beautiful sunny days ahead.
  • Also in Dubuque is the Sunset Ridge Winery. The winery is situated on the bluffs overlooking the Mississippi River, and their tasting room makes for a stunning place to sit and sip wine.

A Great Galena Winery Tour for 2020

Visit our Top-Rated Galena Bed and Breakfast

Located just steps off Main Street in beautiful Downtown Galena, you’ll find an old restored Jail turned luxurious Bed and Breakfast. Jail Hill Inn is the only luxury property of its kind in Galena. Awaiting in your room upon arrival will be chilled champagne and a box of signature chocolates, and that’s just the beginning!  Each evening from 5 – 7 pm, we host a delicious wine and appetizer hour, followed by nightly treats like freshly baked cookies. Each morning, you’ll be treated to a scrumptious 3-course breakfast, and some of the best hospitality you’ll ever experience.

Our guest rooms are filled with luxury amenities and those added touches you crave, like buttery soft Comphy brand linens, plush Frette bath towels and signature bathrobe, premium Bluetooth sound systems that are fully customizable to your preferences, and Aveda bathroom products. Sink into a luxurious bath, unwind in a steam shower, or crawl into our cozy and plush beds. It’s all waiting for you. All you have to do is book a room at the Jail Hill Inn, Galena’s finest Bed and Breakfast, today!


10 Things You Simply Must do in Galena This Winter

10 Things to do in Galena This WinterHave you ever visited Galena during the winter? It’s a wonderful place to visit, even when there’s snow on the ground!  There are plenty of delightful things to do this winter, and we have a great guide for you. Head out on a cross country skiing adventure, explore our vibrant and historic downtown, or sit back and savor the luxurious accommodations found at our Galena Bed and Breakfast.

Galena has long-been a popular getaway destination for those living in or around the Chicago area, and these winter months should be no different. Even if you don’t love spending time outside during the winter, the chance to stay at our romantic Inn is more than worth the time it takes to get here. Your day will start with a delicious breakfast, but that definitely isn’t the end of our award-winning hospitality.  In the afternoon, join us for a delicious wine and cheese hour, along with some delicious fresh cookies, hot from the oven. Come see it for yourself, and book a room at our Galena Bed and Breakfast today. Continue reading

The 7 Best Places for Wine Tasting in Galena

Go Wine Tasting in Downtown GalenaGalena is the perfect getaway destination, especially if you’re looking to do a little wine tasting! It’s a town built with such historic, small-town charm, and has something to offer a spectrum of visitors. Galena’s picturesque and quiet streets are filled with quaint shops and boutiques, gourmet restaurants, spas, and wineries. Even better, all of this and more is easily attainable, as Galena is only a one-tank trip from many large Midwest cities.  Throughout the year, there are a variety of events that draw wine lovers to Galena, and numerous wine bars and wineries open for wine tasting, which allows visitors to keep the drinks flowing throughout the remainder of the year.  Book your room at our beautifully renovated and award-winning Galena Bed and Breakfast, and sip your way through Galena’s best wines. Continue reading

10 Ridiculously Fun Things To Do in Galena in 2019

10 Things to do in Galena in 2019Are you looking for a fun getaway destination? Look no further!  We love our little town of Galena and have some great ideas for all the fun things to do in galena this year, topped off, of course, with a stay at our luxury Bed and Breakfast.

It’s hard to believe sometimes, but after just over 3 years in business, Jail Hill Inn has seen incredible success.  We were named Business of the Year by the Galena Chamber of Commerce, we earned a near-perfect score from Select Registry, and perhaps better yet, TripAdvisor named us the #1 Bed and Breakfast in the United States, and the #2 Bed and Breakfast in the world. Those are all incredible honors, and it has earned us quite a bit of positive press in local and regional media outlets. We’re so grateful for all of our guests over the years that have made this possible, and who continue to stay with us at our Galena Bed and Breakfast. We truly wouldn’t be here without you!  But, that also means we’re seeing a lot of recent reservations, and rooms are booking up quickly both now and into the summer and fall of 2019, especially on those busy and coveted weekends.  If you want to get away to Jail Hill Inn in 2019, you should consider booking your getaways now, and taking advantage of our availability while we still have it. Continue reading

Plan the Best Romantic Getaway to Galena

romantic getaway in Galena, IllinoisDo you find yourself dreaming of a relaxing and romantic getaway, to help pass the time during these cold winter months? Valentine’s Day is just around the corner, so we can think of no better time to plan a romantic getaway than right now.  We have the perfect place in mind for you, too.  Our luxury Bed and Breakfast, just off Main Street in Galena, is the top choice for romantic lodging.  Let us do all the work for you, so you can spend your time relaxing and focusing on enjoying your time together.  Romance is our business, and no one does it better.  Book a romantic getaway with us this winter, and enjoy a restful stay at Galena’s top Bed and Breakfast.  Continue reading

Wine and Hot Air Balloons: Two Great Events in Galena

Summer Events in Galena, IllinoisAs we head into the warmer summer months, things are starting to heat up here in Galena–both literally and figuratively.  The summer months are packed with plenty of fun activities and events.  Whether it’s getting outside for a hike, paddling down the picturesque Galena River, shopping along Main Street, celebrating at festivals, or sampling delicious wines, Galena truly is a town that has it all.  This June you can soar to new heights in a hot air balloon, or stay on the ground and sample the finest food and wine around.  Whatever it is you want to do, you won’t find better accommodations than those at Jail Hill Inn, downtown Galena’s newest luxury Bed and Breakfast. Book your summer getaway with us today! Continue reading

Winter Activities to Enjoy in Galena

Winter Activities to Enjoy in Galena, IllinoisWhether you’re looking for a little outdoor recreation, or the perfect excuse to curl up and get cozy with the one you love, there are plenty of reasons to visit Galena this winter.  During the snowy winter months, Galena transforms into a picturesque wonderland, complete with snow-covered hills and valleys and charming old-world architecture.  Winter activities are plentiful in Galena, ranging from skiing, snowboarding, and sleigh rides, to candlelit hikes and romantic dinners.  With far less crowds than the rest of the year, winter is arguably one of the best times to plan a getaway to our luxurious Bed and Breakfast in downtown Galena.  Book your stay with us today! Continue reading

10 Ways to Enjoy a Romantic Getaway in Galena

Romantic Getaway Galena, IllinoisThese crisp, fall months practically beg for us to curl up indoors, hidden away from the harsh elements outside.  It’s the perfect time to curl up with someone special and focus on romance.  In the Midwest, there’s one romantic getaway destination that outshines the rest.  Galena, a charming small town not too far away from the Midwest’s big city centers, imbues a sense of romance around every street corner and in every restaurant and shop.  Spend your days browsing the towns historic buildings or boutique shops in downtown Galena, sipping wine at regional wineries, and taking in the magnificent scenery.  No matter how you choose to spend your time, there’s no better place to spend a romantic getaway in Galena than at our luxurious Bed and Breakfast. Continue reading

Plan the Best Romantic Getaway This Summer

Romantic Getaway Galena, IllinoisWhen people in the Midwest look for a romantic getaway destination, Galena is often the go-to place. Couples all across the Midwest are discovering Galena’s small town, romantic charm.  There is no doubt that love is in the air in Galena, a town practically built for the romantic in all of us. Galena is easily accessible, too, considered a “one-tank” getaway destination from several major cities, including Chicago & Milwaukee.  Book your room at our newly renovated, luxury Bed and Breakfast, and experience the romance of Galena this summer.

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