Seasonal Hill Country Getaways in Fredericksburg

Hit the road and take advantage of the perfect Texas Hill Country destination—as summer becomes fall and the holiday season follows—on a weekend or midweek getaway to Fredericksburg, west of Austin and San Antonio.

While school’s already set to start up again, there are still three distinct seasons of fun, excitement and things to see and do in Fredericksburg, the heart of the Texas Hill Country, throughout the last five months of 2022.

Situated four hours west of Downtown Houston, Fredericksburg welcomes visitors with a relaxing getaway filled with unique and different events, happenings, and fun throughout the rest of the year. 

Seasonal Events & Fun Through 2022

From late summer though the holidays, Fredericksburg is the perfect home base for one or more Texas Hill Country getaways, from the end-of-summer grape harvest and grape stomps, through the major outdoor destination fall festivals, and to the launch of the holiday season in its historic and charming downtown.

Grape Stomp at Perdenales Cellars near Fredericksburg, Texas | Photo courtesy of Fredericksburg CVB

Texas Wine Country in August

In August, Texas Wine Country comes alive with the activities and bustle of grape harvest season and the month is closed out with the longest continuous county fair in Texas—the Gillespie County Fair, now in its 134th year.

• Texas Wine Country Grape Harvest Events & Experiences – As summer begins winding down, the Hill Country’s grape harvest season kicks into high gear. This is your chance to participate in your very own grape stomp at special public events at select wineries (literal “stomping grounds,” perhaps?), along with other season-ending tours, tastings, festivals, and more at the region’s 50+ wineries. Learn more or get free planning info.
• 134th Annual Gillespie County Fair – Texas’ longest running county fair returns with four days packed with events and entertainment for all ages from Thursday, August 25 to Sunday, August 28, 2022. Visitors are welcomed as locals to enjoy the wide array of activities, including the Gillespie County Fair Parade down Main Street (Friday, August 26, 2022 at 10am), a queens contest, carnival and midway games, more fair food you can imagine, livestock judging, agricultural and household exhibits, arts and crafts, antique tractor shows, live music and dancing, live pari-mutuel horse racing, and more. Learn more or get free planning info.

Fredericksburg’s four-day Gillespie County Fair happens in late August every year. | Photo courtesy of Fredericksburg CVB

Long Labor Day Weekend in September

September is marked by the long Labor Day Weekend—the unofficial end of the summer season complete with live music, shopping, and plenty of family-friendly fun. But the whole month is a great time to visit and explore the town’s parks, shopping, museums, wineries (whose festivals continue into the month), and more.

• Labor Day Weekend in Fredericksburg – The final getaway week of summer—from Friday, September 2 through Labor Day, Monday, September 5, 2022—is chockfull of entertainment and fun. Grape stomps and other wine events carryover from August, but visitors can also cash in on Fredericksburg’s always stellar shopping, art gallery receptions, tasty restaurants, historical museums and installations, fun in the great outdoors, and more. Learn more or get free planning info.
• Midweek Stays & Weekend Visits – Fredericksburg’s mainstay draws like the outdoors, dining, live music, art, and more remain a constant appeal in September. Visitors staying Monday through Thursday will find savings on accommodations, more individualized attention at local shops and wineries, and more perks to be found when life moves at a slower speed. Learn more or get free planning info.

Larry Jackson Fine Art & Antiques in downtown Fredericksburg, Texas | Photo courtesy of Fredericksburg CVB

Food & Drink Events in October

October is the apex of Fredericksburg’s fall festivals, headlined by the town’s famous Oktoberfest and the Fredericksburg Food & Wine Fest. 

• Oktoberfest 2022 in Fredericksburg – Technically kicking off on Friday, September 30, 2022, Fredericksburg’s beloved Oktoberfest lasts the full weekend through Sunday, October 2, 2022. Celebrating the region’s well-established German heritage, the three-day, family-friendly event happens at downtown’s Marktplatz, with five stages of continuous oompah music, arts, crafts, shopping, a children’s area, 50 varieties of beers, Texas Wine Country selections, great food and fun, and more. Advance planning is an absolute must. Learn more or get free planning info.
• 31st Annual Fredericksburg Food & Wine Fest – Texas’ OG food and wine event returns on Saturday, October 28, 2022, showcasing the Hill Country’s award-winning Texas wines and impressive culinary scene. The Fredericksburg Food & Wine Fest also features Texas-made specialty partners, Texas gourmet chefs performing live demonstrations, live entertainment, a silent auction, and more. Move quick and take advantage of special ticketed weekend dinners and brunch. Advance booking and planning are recommended. Learn more or get free planning info.

Oktoberfest at the Marktplatz in downtown Fredericksburg, Texas | Photo courtesy of Fredericksburg CVB

Holiday Season in November & December

Once October wraps, the arrival of November marks the start of Fredericksburg’s holiday season, which is particularly known for world class holiday shopping, a nightly lighting countdown, and great festive entertainment.

Christmas shopping on Main Street in downtown Fredericksburg, Texas | Photo courtesy of Fredericksburg CVB

Perks, Plusses & Benefits of Midweek Visits

While a weekend getaway to Fredericksburg has nonstop appeal, repeat visitors frequently swear by the magic of midweek visits. Adding an element of ease and relaxation, midweek visits offer unique perks that are often trickier to find on the bustling Friday to Sunday at the popular Hill Country destination.

• Score the Best Prices on the Best Place to Stay – Fredericksburg boasts a wide variety of lodging options, including locally owned boutique accommodations, national hotel chains, small inns, vacation rentals, guesthouses, traditional bed and breakfasts, and more. All of them offer savings during the quieter weekdays—even during most peak weeks of the season. Explore places to stay in Fredericksburg or access free planning info.
• Indulge in Personalized Experiences at Local Wineries – Located in the epicenter of Texas Wine Country, Fredericksburg is the best spot to explore more than 50 wineries in the local county, plus another 50+ across the Texas Hill Country. The award-winning wine producers have won accolades from across the globe. And midweek visitors find that they’re able to engage with vinters on a deeper level, have longer discussions about the varietals, and essentially have a more customized, one-on-one experience than may be hard to find during a busier weekend visit. Learn more about Fredericksburg area wineries or access free planning info.
• Enjoy the Relaxed Pace while Shopping – With good reason, shopping is one of the primary reasons that many visitors make the trip to Fredericksburg. Downtown is noted for its staggering collection of home décor and women’s fashion ranging from vintage to upscale contemporary (it’s never too early to shop for 2023’s Rodeo season, y’all). Plus shoppers will discover handmade jewelry, antiques, artwork, gifts, and more. While the shopping opportunities are strong every day of the year, midweek shoppers can take advantage of the quieter stores to enjoy increased hands-on assistance, personal connections with the shopkeepers, and more chances to gain local insights.

Learn more about a midweek escape to Fredericksburg or explore free planning info.

Odonata Escape

The Hangar Hotel

Blacksmith Quarters
Photos courtesy of Fredericksburg CVB

Start Planning Now

Start planning your summer, fall or holiday getaway to the Texas Hill Country on VisitFredericksburgTX.com or request free visitor information. When you arrive in town, make the Visitor Center your first stop for extra tips, guidance, and expert advice for making the most of your visit.

Wine Tasting at Perdenales Cellars near Fredericksburg, Texas | Photo courtesy of Fredericksburg CVB

This article was sponsored by the event organizer. Per our advertising and sponsorship policy, we only accept sponsored content from organizations that meet our editorial standards and truly present a valuable activity, event, resource or destination for residents and visitors across the greater Houston area. Advertising revenue helps support 365 Things to Do in Houston, and our contributors, allowing us to expand our coverage of activities and events around the Houston area. Learn more about promoting your event or business.