Extended Weekend Getaways
Celebrating at the Mile High Kit Festival. Photo – Todd Bush
For me, summer doesn’t begin with a date; it begins with a decision to go. Over the years, I’ve learned that how you start the season matters. From wandering the storybook streets of Helen, Georgia, to soaking in the coastal charm of North Myrtle Beach, I’ve seen firsthand how an easy escape can shift your mindset from busy to present.
This year, with America 250 on the horizon and Route 66 celebrating its centennial, there’s even more reason to kick off summer with purpose and a sense of place.
Summer is more than a season. It’s a reset button.
And there’s no better way to press it than with an Extended Weekend Getaway, especially one that blends family fun, meaningful experiences, and a touch of Americana.
Highlights: Kick Off Summer the Smart Way
- Best family-friendly destinations to start summer with energy, ease, and meaning
- Festivals, events, and hidden gems that create instant “this feels like summer” moments.
- How to plan an extended weekend getaway that’s low-stress, high-impact, and memory-filled
Why Kicking Off Summer Matters
We celebrate beginnings for a reason.
A summer kickoff trip:
- Marks a transition from routine to freedom
- Creates shared memories early in the season
- Sets the tone for how you’ll spend your time
Instead of letting summer “just happen,” you step into it intentionally.
Why an Extended Weekend Getaway Works So Well
Not every family can take a week-long vacation in June. That’s where the extended weekend shines.
Three or four days gives you:
- Enough time to relax without overplanning
- A manageable budget and schedule
- A chance to test-drive a destination before a longer return trip
Think of it as your summer preview—with real memories attached.
Family-Friendly Summer Kickoffs Worth Planning
Alpine Charm in Helen, Georgia
Alpine Helen Songwriters Festival – Photo Alpine Helen White County Convention and Visitors Bureau
Helen surprised me the first time I visited. A Bavarian-style village tucked into the North Georgia mountains wasn’t what I expected, and it was so unique for the area.
As the season shifts into summer, Alpine Helen blends music, storytelling, and mountain charm into the Alpine Helen Songwriters Festival, April 24-26, 2026.
The village transforms into a multi-venue listening room, where award-winning songwriters from Nashville and across the South perform the songs they’ve written for major artists, and share the personal stories behind them. “The Songwriters Festival offers something truly special, you’re not just hearing the music, you’re hearing the stories behind it, in a setting that makes the entire experience feel personal and unforgettable.” says Jerry Brown, Executive Director, Alpine Helen-White County Convention and Visitors Bureau.
What makes this especially unique is the format: instead of large-scale performances, audiences hear stripped-down acoustic sets paired with storytelling. Often from writers behind chart-topping songs for artists like Tim McGraw and Luke Bryan.
Families can pair music with:
- River tubing
- Easy hikes
- Walkable dining and shops
It’s immersive without being overwhelming.
Beech Mountain, North Carolina
Mile High Kite Festival
As the Highest Town in Eastern America at 5506 feet, Beech Mountain, NC, literally hosts one of the most high-flying kite experiences in the country.
The Mile High Kite Festival, May 23 from 10 am – 4 pm, transforms the mountain into a sea of floating color with whimsical kites soaring against a mountain backdrop. It’s simple, joyful, and refreshingly low-cost.
Consistent mountain winds make for ideal flying conditions, while the cool summer temperatures create a refreshing escape from the heat below.
The event is free, and complimentary kites are provided for kids 12 and under to decorate. (while supplies last)
Coastal Traditions in North Myrtle Beach
Delicious Blue Crabs -Photo Robin O’Neal Smith
In nearby Little River, you can attend the Blue Crab Festival May 16-17, 2026. It is one of the largest festivals in the Southeast.
It brings:
- Fresh coastal flavors
- Waterfront views
- Family-friendly energy
Bare feet in the sand, the smell of seafood, and live music humming in the background, it’s the kind of kickoff that signals summer has officially begun.
Hendersonville, North Carolina
Garden Jubilee
Garden Jubilee Photo – Jared Kay
Is gardening your thing? Kick off summer with the Garden Jubilee. This outdoor garden show is one of the largest in the Southeast. Main Street transforms into a seven-block oasis of plants and gardening supplies with approximately 150 vendors on Memorial Day Weekend.
“This is such a beloved and time-honored event that everyone waits for in Hendersonville,” says Terrye Jacobs, Hendersonville events coordinator.
For families, it’s interactive and educational:
- Gardening demos
- Kid zones
- A walkable downtown filled with color
Kinetic Sculpture Race – Baltimore, Maryland
Kinetic Sculpture Race
This is what happens when creativity runs wild.
Pedal-powered sculptures tackle land and water in a race that’s part art show, part obstacle course. Kids love the spectacle, and adults appreciate the ingenuity.
The Kinetic Sculpture Race on May 2 is hosted by the American Visionary Art Museum.
America 250 + Route 66: A Meaningful Summer Kickoff
Tulsa’s Capital Cruise celebrating Route 66.
Tulsa & Oklahoma City, Oklahoma
As America approaches its 250th Anniversary, and Route 66 celebrates its centennial, destinations like Tulsa and Oklahoma City offer more than a getaway, they offer context.
In Tulsa:
- On May 30, 2026, Tulsa will celebrate 100 years of Route 66 with the Route 66 Capital Cruise, an ambitious GUINNESS WORLD RECORDS® attempt for the largest classic car parade ever held! The fun extends throughout the weekend, turning it into a massive birthday bash.
In Oklahoma City:
- Visitors can explore Route 66’s once-in-a-century milestone while also stepping inside The Cowboy: An Immersive Journey at the National Cowboy & Western Heritage Museum, a fully interactive experience that brings the stories, landscapes, and spirit of the West to life.
“Oklahoma City is where you can step inside the story of the American West and then celebrate the legacy of Route 66 in the same trip,” said Lindsay Vidrine, Chief Marketing Officer, Greater Oklahoma City Chamber.
This is where a summer trip becomes a story about America itself.
More Unique Summer Kickoff Ideas
Summer Nights Car Show in Dawsonville.
- Dawsonville, Georgia – June 12, the Summer Nights Car Show Series at the Georgia Racing Hall of Fame will bring together vintage cars, racing enthusiasts, and live entertainment with a high-octane celebration of speed, heritage, and Southern culture rooted in the town’s identity as the birthplace of NASCAR.
- Jeffersonville, Indiana – Beatles music fills the riverfront at Abbey Road on the River over Memorial Day weekend. It is the world’s largest Beatles-inspired music festival.
- Chicago, Illinois – A refined kickoff with Champagne at the Waldorf Astoria’s Clicquot Courtyard begins May 28. This reservation-only experience pairs Veuve Clicquot with elevated charcuterie, set to live music. Seatings are available Thursdays through Sundays.
Each offers a different way to say: “Summer starts now.”
Why Families Should Make This a Tradition
Abbey Road on the River in Jeffersonville, Indiana.
The magic of a summer kickoff isn’t just the destination.
It’s the tradition.
Kids remember:
- The first beach day
- The first festival
- The first ice cream of the season
And over time, those “firsts” become the story of your family.
If You Go: Planning Your Summer Kickoff
Best Timing:
Memorial Day weekend through mid-June offers peak kickoff events with smaller crowds than July.
What to Pack:
- Lightweight layers (especially for mountains)
- Comfortable walking shoes
- Reusable water bottles
- A small daypack for festivals
Booking Tip:
Reserve early for festivals and holiday weekends—especially in destinations like Helen and North Myrtle Beach.
Pro Tip:
Pair one anchor event (festival, attraction) with free time. Overpacking your itinerary defeats the purpose of a kickoff escape.
Frequently Asked Questions About Summer Kickoff Travel
When is the best time to take a summer kickoff trip?
Memorial Day weekend through mid-June is ideal. You’ll find festival energy, warm weather, and fewer crowds compared to peak July travel.
Where can families go for a quick summer getaway?
Look for destinations within a 3–5-hour drive or a short flight. Coastal towns, mountain retreats, and festival-driven small cities are perfect for extended weekends.
What are affordable summer getaway ideas for families?
Choose destinations with free or low-cost events such as festivals, parks, and outdoor activities. Places like Beech Mountain and Hendersonville offer high value without high prices.
How far in advance should I book a summer trip?
For popular kickoff weekends like Memorial Day, book 6–10 weeks in advance. For smaller destinations, 3–4 weeks may still work.
What makes a great summer kickoff destination?
The best destinations combine:
- One anchor experience (festival, beach, event)
- Plenty of downtime and flexibility
- A sense of place or story (history, culture, or local flavor)
