September 3, 2026
If you're searching for the best things to do in the Tri-Valley this Labor Day Weekend, there are plenty of ways to enjoy the final stretch of summer close to home. From one of Pleasanton's biggest annual traditions to live music, local wineries, outdoor adventures, and Downtown Pleasanton and Livermore, the long weekend offers something for almost everyone.
Labor Day falls on Monday, September 7, 2026, creating a three day weekend that's perfect for exploring the Tri Valley. Whether you live in Pleasanton, Livermore, Dublin, or elsewhere in the East Bay, you don't have to travel far to find something fun to do.
At Elation Real Estate, we know that loving where you live is about much more than the home itself. The local events, restaurants, wineries, parks, and community traditions are all part of what makes the Tri Valley lifestyle so special. Here are some of the best activities and events to add to your Labor Day Weekend 2026 plans.
Some of the best things to do in the Tri-Valley for Labor Day Weekend 2026 include attending the 160th Scottish Highland Gathering & Games in Pleasanton, celebrating at the Concannon Estate Block Party, listening to live music at Livermore Valley wineries, seeing a concert at Wente Vineyards, exploring Downtown Pleasanton or Downtown Livermore, and spending time outdoors at one of the area's parks and trails.
Alameda County Fairgrounds, Pleasanton
September 5 and 6, 2026
One of the biggest Labor Day Weekend events in Pleasanton returns to the Alameda County Fairgrounds for its 160th year.
The Scottish Highland Gathering & Games is a longtime Bay Area tradition celebrating Scottish culture with Highland athletic competitions, music, dancing, food, and entertainment. It's one of those events that brings something completely different to Pleasanton and has become a Labor Day Weekend tradition for generations of visitors.
Families, groups of friends, local traditions, and anyone looking for a classic Pleasanton Labor Day Weekend experience.
4590 Tesla Road, Livermore
September 5 through 7, 2026 | 11:30 AM to 5:00 PM
If your ideal Labor Day Weekend includes live music, local food, and Livermore Valley wine country, the Concannon Estate Block Party is an easy addition to the weekend.
The celebration takes place all three days of Labor Day Weekend on the Estate Lawn at Concannon Vineyard. Live music runs from noon to 4:00 PM daily, with SugarBear performing Saturday, LunaFish on Sunday, and Michelle Lambert closing out the weekend on Monday.
Guests can enjoy wines from Concannon Vineyard and Cuda Ridge Wines, local food, vineyard views, and plenty of room to relax outside. Admission to the community event is free, and children are welcome.
Wine lovers, families, groups of friends, live music, and a relaxed afternoon in Livermore Wine Country.
1356 South Livermore Avenue, Livermore
September 5, 2026 | 12:00 to 4:30 PM
Spend Saturday afternoon among the vines at Retzlaff Vineyards, where Chris Rogers will perform live music and Tasteful Catering will be serving food.
Visitors can come for a wine tasting or enjoy a bottle picnic while listening to music in the vineyard. Reservations are appreciated, and the winery welcomes children and well behaved dogs.
It's an easy way to experience the laid back side of the Livermore wine experience without needing to plan an entire day around a formal event.
Couples, groups of friends, wine lovers, and anyone looking for a relaxing Saturday afternoon.
5050 Arroyo Road, Livermore
September 5, 2026 | 6:00 PM
Keep Saturday going with an evening of music at Wente Family Vineyards.
Billy Nation, a Billy Joel tribute band, takes the stage during Wente's summer concert series. Guests can settle onto the outdoor concert lawn with low back chairs or blankets while enjoying music alongside Wente wine, beer, cocktails, and dinner concessions.
It's a fun way to turn a day exploring Livermore into a full evening out.
Date night, music lovers, groups of friends, and anyone looking for a lively Saturday night.
2271 South Vasco Road, Livermore
September 5, 2026 | 7:00 to 11:00 PM
For something completely different, Longevity Wines is hosting its first Bollywood Night on Saturday evening.
The celebration features a live DJ playing Bollywood music, dancing, a food buffet catered by Kabila, and wine. Admission includes access to the buffet and a glass of wine.
It's one of the more energetic options on the Labor Day Weekend calendar and a fun choice if you're looking to trade a quiet wine tasting for a night of music and dancing.
Groups of friends, couples, dancing, and anyone looking for a lively Saturday night in Livermore.
2271 South Vasco Road, Livermore
September 6, 2026 | 1:00 to 4:00 PM
If Sunday calls for something more relaxed, head back to Longevity Wines for an afternoon Jazz Jam Session.
Members of the Livermore Jazz Society and Las Positas College Jazz Band come together for an informal afternoon of live jazz. Musicians and singers are invited to participate, while everyone else can enjoy the performances with a glass of local wine.
Jazz fans, wine lovers, couples, and anyone looking for a slower Sunday afternoon.
Main Street, Pleasanton
Not every Labor Day Weekend activity needs a ticket or reservation. Spending a few hours in Downtown Pleasanton is an easy way to enjoy the long weekend at your own pace.
Start with coffee or brunch, stroll along Main Street, browse local boutiques, and stay for dinner or drinks. Downtown's combination of restaurants, shops, historic character, and community atmosphere is one of the reasons Pleasanton continues to be such an appealing place to call home.
You can also pair a morning or evening downtown with the Scottish Highland Gathering & Games for a full day in Pleasanton.
Brunch, shopping, date days, families, and a relaxed afternoon close to home.
First Street and surrounding Downtown Livermore
If you're already heading to Livermore for wine tasting or live music, leave some time to explore Downtown Livermore.
The pedestrian friendly downtown district brings together restaurants, wine bars, craft beer destinations, shops, entertainment, and public spaces. You can start with coffee, explore the shops, stop for lunch, and then head into Livermore Valley Wine Country later in the afternoon.
If food is the main event, check out our guide to the best restaurants in Downtown Livermore for more ideas.
Foodies, couples, shopping, casual afternoons, and anyone who wants to combine downtown and wine country in one day.
Sometimes the best way to spend a long weekend is simply to get outside.
Pleasanton, Livermore, Dublin, and the surrounding communities offer plenty of parks, trails, and open spaces for hiking, walking, biking, or enjoying a picnic.
Pleasanton Ridge Regional Park is a favorite for sweeping views and miles of trails, while Sycamore Grove Park in Livermore offers another scenic place to walk or bike. Nearby Sunol Regional Wilderness is also worth exploring if you're looking for a longer outdoor adventure.
Hikers, families, outdoor lovers, active weekends, and anyone looking for a break from the crowds.
You don't need to fill every hour of the three day weekend with scheduled events.
Pick up lunch from a favorite local restaurant and plan a picnic, spend an afternoon by the pool, visit a winery you've never tried before, explore a new Tri Valley neighborhood, or simply gather friends and family for a backyard barbecue.
One of the best parts about living in the Tri -Valley is having so many different experiences within a short drive.
Labor Day is Monday, September 7, 2026. Labor Day Weekend runs from Saturday, September 5 through Monday, September 7.
One of the biggest events is the 160th Scottish Highland Gathering & Games, taking place September 5 and 6 at the Alameda County Fairgrounds in Pleasanton.
Livermore has several events scheduled throughout the weekend, including the Concannon Estate Block Party, live music at local wineries, Billy Nation at Wente Vineyards, Bollywood Night at Longevity Wines, and additional wine country experiences.
Yes. The Scottish Highland Gathering & Games is a popular option, while Concannon's Estate Block Party is open to the community and welcomes children. Families can also explore Downtown Pleasanton, local parks, hiking trails, and other outdoor spaces.
Spend the day exploring Downtown Pleasanton or Downtown Livermore, go hiking at Pleasanton Ridge, visit a local park, plan a picnic, try a new restaurant, or explore Livermore Valley wine country.
Labor Day Weekend offers a little bit of everything that makes the Tri Valley special.
In a single weekend, you can experience a major community tradition in Pleasanton, spend an afternoon among Livermore's vineyards, listen to live music, explore two vibrant downtown districts, enjoy local restaurants, or escape into miles of East Bay open space.
It's this combination of community, recreation, dining, wine country, and everyday convenience that makes Pleasanton, Livermore, Dublin, and the surrounding communities such enjoyable places to live.
At Elation Real Estate, we understand that choosing where to live is about much more than bedrooms, bathrooms, and square footage. It's about finding a community where you can enjoy your everyday life.
Whether you're considering buying or selling a home in Pleasanton, Livermore, Dublin, San Ramon, Danville, Alamo, or elsewhere throughout the East Bay, our team combines local knowledge with personalized real estate guidance to help you navigate your next move with confidence.
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