Best Healdsburg Events for Second Homeowners

There’s something magical about being more than a visitor in a place like Healdsburg. When you own a second home here, you’re not just weekend tripping—you’re part of the rhythm, local traditions, and heartbeat of a small-town community that knows how to celebrate life. From quirky local traditions to heartwarming family events and unforgettable holiday charm, Healdsburg offers year-round moments that second homeowners can truly make their own. Here’s our handpicked list of the Best Healdsburg Events for Second Homeowners—and why each one makes owning a second home in this wine country gem even more rewarding.

Best Healdsburg Events

1. Healdsburg Twilight Parade & Future Farmers Country Fair

📅 Parade: At the end of May
📍 Downtown Healdsburg & Rec Park

There’s no better way to feel the soul of Healdsburg than lining the streets for the annual 4H Twilight Parade. This isn’t just a float-and-wave affair—it’s a celebration of community spirit, agriculture, and small-town pride. With local kids, farmers, and school bands strutting their stuff, you’ll feel instantly connected to the town’s heritage.

The parade kicks off the Healdsburg Future Farmers Country Fair, where 4H and FFA kids showcase animals they’ve raised, and local families gather for games, live music, a circus, and indulgent fair food.

Families love staying in full homes versus hotels during summer holidays. This is your opportunity to offer them a cozy, backyard-equipped rental that feels like a home away from home.

• Average daily rate in July: ~$604
• Monthly Revenue Potential: Up to $9,084

Depending on size and location, you could net $3,500–$5,000 if you rent for just the holiday week.

2. The Rotary Club of Healdsburg Easter Egg Scramble

📅 During mid April
📍 Fitch Mountain School

Bring the kids or grandkids to this charming community tradition where inclusivity takes center stage. The Rotary Club’s annual Easter Egg Scramble welcomes all abilities and ages, with over-the-top egg hunts, a free bike raffle, and plenty of photo ops. Did you know our very own Realtor Emily Martin is an active Rotarian with the Healdsburg Rotary Club? That’s right, she’s been a Rotarian since 2020 when moving to Healdsburg and could not be more proud. Her Grandfather was in the Founding Chapter #1 of the Rotary Club in Chicago, IL 

Families love staying in full homes versus hotels during summer holidays. This is your opportunity to offer them a cozy, backyard-equipped rental that feels like a home away from home.

• Average daily rate in July: ~$604
• Monthly Revenue Potential: Up to $9,084

Depending on size and location, you could net $3,500–$5,000 if you rent for just the holiday week.

3. Healdsburg Turkey Trot

📅 On Thanksgiving Day
📍 333 Center Street

The Turkey Trot is how Healdsburg earns its second helping of stuffing. This casual, festive 5K draws both locals and out-of-towners, with a scenic loop through Healdsburg’s charming neighborhoods and views of Fitch Mountain.

It’s also a feel-good affair, raising funds for the Drew Esquivel Scholarship Fund, helping local high school scholar-athletes chase their college dreams.

Thanksgiving is one of the most lucrative times for rentals—multi-generational families travel to wine country and need space. Homes with kitchens and dining areas are especially desirable.

• Average daily rate in November: ~$604
• Occupancy Rate: 60–70%

Renting for the long weekend (Wed–Sun) can bring in $2,400–$3,500.

🎆 4. 4th of July Kids Parade & Duck Dash

📅 July 4
📍 Healdsburg Plaza

Start your Independence Day with a red, white, and blue bang at the beloved Kids Parade. Local children dress up in star-spangled outfits and march through the Plaza—parents and grandparents lining the streets with cameras ready.

Then comes the famous Duck Dash, where rubber duckies race for glory in Fountain Square, raising money for local causes.

Holiday travelers seek cozy rentals to gather, shop, and celebrate. Bonus for second home owners in Healdsburg: if your place has a fireplace or wine cellar, the price rate can increase to your favor!

• Average daily rate in December: $700–$900
• Occupancy Rate: Up to 76%

You could earn $2,100–$3,600 in just a weekend.

5. Rotary Crab Feast, December 

📅 December (Date TBA)
📍 Villa Chanticleer

Unlimited local Dungeness crab. Healdsburg wines. A raucous auction with hilarious MCs. The Rotary Crab Feast isn’t just dinner—it’s a cornerstone of winter social life in Healdsburg. Funds go to scholarships, senior lunches, domestic violence shelters, and more.

Spring break travelers + family-friendly events = prime time for bookings. Homes with yards are especially appealing.

• Average daily rate in April: ~$550
• Weekend rental income: $1,500–$2,200

6. Merry Healdsburg Tree Lighting

📅 Beginning of December
📍 Healdsburg Plaza

Get swept up in a Hallmark movie moment. As the sun sets on the Plaza, the community gathers for live carols, carriage rides, mulled wine, and the lighting of the town’s iconic Christmas tree.

It may be off-season, but the community vibe draws locals and extended family into town, creating niche demand.

• Average daily rate in December: ~$500
• Potential Earnings: $1,200–$1,800 for a short 2-night stay

If you are planning to do fun activities during the December holidays, here is a guide with the best activities to enjoy with the family in that special time of the year.

Why These Events Matter for Second Homeowners

Beyond the events, Healdsburg boasts year-round tourism, stunning natural beauty, award-winning wineries, and a culinary scene that rivals Napa. It’s not just about the Healdsburg events for second homeowners, it’s about finding the right place for your needs.

By timing your short-term rental availability with these key events, you can maximize your home’s potential and help visitors experience the very best of Healdsburg, just like a local.

Why choose Realtor Emily Martin?

Emily has called California home for over a decade and likes to think of herself as a California “native”. Learning at a young age from her mother Linda K. Martin, a top-producing real estate agent for 40+ years, Emily has been immersed in Real Estate all of her life. As a homeowner in her early 20s in Manhattan’s Gramercy Park, followed by San Francisco, and now Healdsburg, Emily understands the intricacies of home ownership in highly sought-after regions such as Manhattan, San Francisco, Sonoma County, Napa Valley, and her beloved hometown of Healdsburg, California. 

Whether you’re buying your dream home, purchasing a second home, selling a cherished property, or investing in the market, I’m here to make your dreams a reality. My extensive luxury experience, attention to customer experience, marketing expertise, hard work ethic, and passion allow me to provide a level of service that is truly distinctive. As we start our journey together, here’s what you can expect: 

Unmatched Luxury Expertise

With a deep-rooted understanding of the luxury market, I bring a wealth of knowledge and insight into luxury goods, sales, and lifestyle. Whether you’re buying or selling, I have the expertise to navigate the world of real estate and the Healdsburg Luxury Homes market.

A Tradition of Excellence

With a family legacy spanning four decades in real estate, excellence is not just a goal, it’s a tradition. I am committed to upholding the impeccable reputation my mother, Linda K. Martin, a top North Shore Chicago agent, has built by delivering nothing short of excellence to my clients. 

Unwavering Dedication & Passion

I am dedicated to your success. From the moment we embark on this journey together, I will provide unwavering support, guidance, and attention to detail, ensuring a seamless and stress-free experience. When asked to describe Emily, the first words that come up with my clients are passionate, energetic, experienced, and dependable. 

Explore the Luxury Lifestyle in Healdsburg’s Wine Country

Luxury real estate is not just about properties, it’s about a lifestyle. It’s about finding the perfect blend of elegance, sophistication, and comfort that feels like you. It’s the feeling you get when you walk into your dream home.

Contact me today at:  [email protected] or 707-926-3200 to begin your extraordinary real estate experience. Together, we’ll create a story worth telling, a life worth living, and a legacy worth building.