A cyclist on an open road at golden hour, Hill Country silhouette on the horizon

Hosted cycling weekends · Wimberley, Texas

Ride the roads that builtthe Hill Country’s reputation.

Trips built on riding and community.

A weekend of good roads and good company.

Wimberley sits in the heart of the Hill Country, where the roads climb, roll, and quiet down to almost nothing. You ride them over a weekend with a small group who takes the sport as seriously as you do.

Between rides you come back to the house. The host rides with you, knows the roads, and keeps a good kitchen. Dinner runs long, and the conversation runs longer.

Hill Country Ride House. Wimberley, Texas.

Ride. House. Gather.

Three things, done properly.

Longhorns grazing in a Hill Country pasture at dusk

01 · Ride

Curated routes

The host picks the roads to fit the group and the day. No two weekends ride the same.

The stone house in Wimberley under a pink evening sky

02 · House

A home base

A comfortable house with a full kitchen, good beds, and room to recover. The host is here the whole weekend.

Wings on the grill at sunset on the back patio

03 · Gather

The table

Dinner Friday and Saturday, breakfast each morning, and fueling on the bike. The table is where the weekend slows down.

“The routes are challenging, but the scenery, food, and local charm make it like a mini vacation.”

Julie · Founders Weekend

Rolling Texas Hill Country at golden hour, layered ridgelines under a warm sky

The riding is the reason

Roads that reward the effort and pay it back in scenery.

Miles with friends

The company is half of it.

Early starts, morning sunrises, memorable rest stops and plenty of time around the pool to rest and relax with friends. The people are the reason the weekends are built the way they are.

Bill with two riders after a daytime charity ride

Bill with two riders finishing a ride after dark

2026 weekends are open. Spots are limited. Wimberley, Texas.

Inquire About a Weekend →

The weekend

Friday afternoon to Sunday midday.

You arrive a guest and leave having ridden roads you'll talk about for a while. Here is how the weekend goes, start to finish, nothing rushed.

Friday

Arrival

Settle in.

You arrive in the afternoon or evening and are greeted with a place for your bike, your assigned room, and where to find your favorite drink. There's a short shakeout ride if your legs want it, an easy spin with no agenda. Dinner is ready to eat as a group around 7:00 PM, or later when you do arrive.

Saturday

The Signature Ride

The reason you came.

The big day. The route is built for the group, and the host rides with you and reads the road as it goes. We stop for a memorable breakfast in Canyon Lake before returning. You come back, clean up, eat a good lunch, and the afternoon is yours to rest and relax. Dinner that night is the best meal of the weekend, and everyone has earned it.

Sunday

Departure

One more, then home.

A final morning ride, shorter and unhurried, the kind that sends you off right.

The house

Where the weekend actually happens.

Between rides, this is home base. A pool to sink into after the long day, good beds for the recovery, and a porch that catches the evening. You settle in Friday and it is yours through Sunday.

The pool and live oaks under a pink and lavender Hill Country sunset

A made-up guest bedroom with warm lamplight

A guest room with leather chairs and a dresser by the window

The pool and back fence line on a clear blue-sky morning

Riders gathered on the covered patio by the pool as the sky turns orange

Full support and community

You ride. Everything else is handled.

Who this is for

If you ride a hundred-plus a week, you already know.

This is for serious recreational riders who put in long miles and own solid equipment. People who want roads worth riding, recovery that actually works, and a community that connects. People in flat cities who are tired of riding the same flat loops.

If you want to feel like a guest in someone's home for the weekend, you're the person we built this for.

From the Founders Weekend

“Amazing hospitality and rides. I look forward to coming back soon.”

Levik

“Routes are challenging, but the scenery, food, and local charm make it like a mini vacation.”

Julie

“Bill, you’ve got a great product and you’re an exceptional host.”

Wayne

After the weekend

The table doesn't close when you drive home.

Ride with us once and you're part of the group. We keep a small, private channel going year-round, the people who have been here, the host, and the roads we're all still talking about.

A private group threadWhere the weekend keeps going, conversations, photos, and ride plans.
Routes worth sharingThe roads you rode, the GPX files, and new ones we find through the season.
First word on next timeReturning riders hear about new weekends before anyone else. Come back when it suits you.

The roads

Roads worth driving to ride.

If you ride flat city loops all week, the Hill Country will feel like a different sport. What climbs, what's smooth, where the traffic is, and why each road earns its place in the weekend.

The terrain, plainly.

This is not flat.

Traffic is light to none on the roads we choose, and we choose them for that reason. Surfaces are mostly good chip-and-seal and clean asphalt, with a few rough stretches we'll warn you about. Bring the climbing gears you'd want for a full day out. The payoff is scenery you don't get anywhere flat.

Out on the roads

You'll have company.

The cattle were here first. Longhorns, the odd calf by the fence line, a herd that barely looks up as you spin past. It is part of why the roads feel like yours for the morning.

Two longhorns grazing in an open field at dusk

Cattle grazing under live oaks on a bright spring day

A cow grazing beside a quiet gravel ranch road

The riding

Three signature routes.

A weekend runs three rides: an easy opener on Friday, the big Saturday loop, and a Sunday ride before you head home. The host builds the exact routes around the group.

Dripping Springs Taco Ride

40

miles

2,500

ft elevation

Rolling Hill Country terrain
Scenic overlooks
Onion Creek crossing
Breakfast tacos
Climbs including Powder Puff Hill

Canyon Lake Signature Ride

55

miles

4,000

ft elevation

Scenic Hill Country roads
Creek crossings
Lunch stop at D’Vine Bistro
Signature climbs including Hammerhead

Wimberley Sunday Recovery Loop

27

miles

1,600

ft elevation

Low traffic Hill Country roads
Sunrise summit
Creek crossings
Coffee and Farmers Market after

Over the weekend

100

miles

7,000

ft climbing

3

rides

Built for the group

No two weekends ride the same.

Routes are personalized. The host rides with the guests and picks the roads based on the group's fitness, goals, and the conditions on the day. You tell us what you're after; we know where to point it.

Service nearby

If the bike needs a hand.

Good shops are close. Trek Bicycle San Marcos and Galaxy Bicycles handle service and support, so a mechanical never ends a weekend.

2026 Season

The Calendar

Founding Season rates hold through the inaugural year. Each weekend is a small group and spots are limited. Tell us which one suits you below.

Jul 17–19

Hill Country Summer Escape

$595per person · Founding Season
Aug 13–15

Creek Crossing Weekend

$695per person · Founding Season
Sep 17–20

Hill Country Fall Kickoff

$695per person · Founding Season
Oct 2–4

Ride & Vine WeekendWine pairings and tastings with a special guest sommelier to guide you.

$895per person · Founding Season
Oct 30–Nov 1

Costumes, Climbs & Cocktails

$695per person · Founding Season

Inquire

Let's Talk About a Weekend.

Spots are limited and we would like to know a bit about who you are before we connect.

We read every note ourselves and reply within a day. Wimberley, Texas. 2026 weekends are open.

Meet Bill, your host →

See the full 2026 season and Founding Season rates in the calendar above.

First name *

Your first name, please.

Last name *

And your last name.

Email *

We'll need an email to reach you.

City *

Where are you riding out of?

How did you hear about Hill Country Ride House?

Tell us a little about your riding, your background and goals

Preferred weekend *

Jul 17–19 · Summer Escape Aug 13–15 · Creek Crossing Sep 17–20 · Fall Kickoff Oct 2–4 · Ride & Vine Oct 30–Nov 1 · Costumes & Climbs Flexible

Pick a weekend that suits you.

Founding Season rates are listed in the calendar. Tell us a bit about you and we'll handle the rest together.

Journal

Notes from the house.

A few words on the town we ride out of, and why it earns the drive.

An open Hill Country road at golden hour

The TownMay 28, 2026

Why Wimberley

People ask why we chose Wimberley. The honest answer is the roads, and then the town gives you every reason to stay the weekend.

Read the note →

The host

Meet Bill.

Hill Country Ride House is one person's idea of a good weekend. Here is who is setting the table.

Bill on a ride in the Hill Country, helmet and shades, a sculpture behind him

Wimberley, Texas

Bill Tipton

Greetings! As your host for the weekend here in Wimberley, I plan the routes based upon your skill level, ride the routes with you, prep and cook the meals you want to eat, and of course share stories of cycling and life. Come join us!

The long way here

I have been riding since I was a kid. Back then a bike meant freedom. It was how I got to baseball practice, how I saw friends, how I learned to count on my own two legs long before I had a car.

Cycling stayed with me through high school and college, where it was mostly how I got around. Then life filled up with work and family, the way it does, and the bike sat quiet for a while.

I found it again years later. My sister Patricia was fighting Multiple Sclerosis at the time, so I signed up for the Houston-to-Austin MS 150 to ride for her and to test myself. What started as a ride for her brought me all the way back.

Since then the bike has taken me a lot of places. The hills of Connecticut, the beaches of Florida, mountain passes in Colorado, gravel roads across the Pacific Northwest. I have raced gravel and run monthly challenge rides with friends in Seattle. When I came home to the Texas Hill Country, I found winding roads, steep climbs, hidden valleys, and the kind of sunrises you remember.

These days the riding is about more than fitness. It is community and exploration and the pull of a road I have not turned down yet. I still love a hard route. I love just as much showing someone roads they would never have found on their own.

Hill Country Ride House brings together the things I care about. The riding, the cooking, the hosting, the stories that come out around a table. Planning the route, putting together a meal after a long day, mixing a drink by the pool, sitting up late in good conversation. The aim is simple. Send people home with a weekend they keep talking about.

I am always learning. I lean on good tools to sharpen the route planning, the training, the nutrition, and the recovery, and I pair them with decades on the bike.

What stays with people is rarely the miles or the elevation. It is the company, the roads, and the Hill Country at its best. You go home with stories worth telling.

I hope you'll join us for a ride.

Riding since childhood. Exploring still.

Miles with friends

The company is half of it.

Early starts, morning sunrises, memorable rest stops and plenty of time around the pool to rest and relax with friends. The people are the reason the weekends are built the way they are.

Come ride a weekend with us in Wimberley.

Inquire About a Weekend →

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