top of page

VIRGINIA WINE COUNTRY BY BIKE

Charlottesville Bike Tours to Wineries & Farms

Ride through Virginia wine country with a closer look at what's growing around you. Ecologically grown wine, vineyard walks, local food, sheep, pollinators, all in a day on two wheels.

AVIF 7.avif

easy-going by design.

That's how guests describe it. They also call out the incredible food, and Jeff's knowledge of ecological grapegrowing and winemaking.

"Works for all levels of riders."

01-easy-going-by-design.webp
02-there-s-a-lot-between-one-winery-and-the.webp

there's a lot between one winery and the next.

Out here, it's rural Central Virginia roads with rolling hills, vineyards, horse country, with Blue Ridge views. Take the time to look around, settle into the ride and notice what's between one stop and the next.

CHOOSE YOUR DAY

3 ways to ride with Shifting Gears.

a public, or private, ride through Virginia wine country with wine tastings, vineyard walks, and a locally sourced lunch and snacks.

VIRGINIA'S ECOLOGICAL WINERY & BIKE TOUR

FLOWER FARMS & THE FUTURE OF FOOD TOUR

a private bike tour visiting Charlottesville's most beautiful flower farm and Central Virginia's largest CSA farm. local eats and your own bouquet to take home.

07-what-guests-remember.webp

PRIVATE & CUSTOM EXPERIENCES

private tours are the way to go if you value a customized experience, or for the intimacy asked for when celebrating a special moment together. from NoVA to Richmond, Charlottesville to 'The Valley'.

09-cta-banner.webp

YOUR GUIDE

there's a reason Jeff notices the sheep.

Before starting Shifting Gears, Jeff worked within all three tiers of wine: grapegrowing & winemaking, distribution, and as a restaurant sommelier & wine educator. He has also spent the past decade working within and around local food systems.

So a vineyard walk with Jeff can move from what's in your glass to the sheep grazing the vineyard, to local food systems, and back to how that all relates to what is in your glass.

03-there-s-a-reason-jeff-notices-the-sheep.webp
04-want-a-little-help-on-the-hills.webp

want a little help on the hills?

Simple to use E-Bikes are available for guests who desire a little help along the way. Charlottesville is rolling hill country.

RIDE AN E-BIKE

Guests invariably appreciate the ease of use, and how using one opens them up to just enjoying the ride.

OR A TRADITIONAL BIKE

If you're here for the cycling, comfortable fitness bikes are available too.

EVERY TOUR. EVERY TIME.

lunch gets local, too.

A seasonal, locally sourced lunch. Not another charcuterie board from the fridge. And don't sleep on our "100% Virginia PB&J," built exclusively by ingredients from Virginia growers and producers. Separating this experience from anything else you'll encounter.

05-lunch-gets-local-too.webp
06-all-you-need-to-bring-is-a-smile.webp

all you need to bring is a smile.

The best cycling routes, wine tastings, locally sourced food, helmets and water bottles, vineyard walks, and ecological education, are all part of the day.

You don't have to guess at mapping a route, figuring out lunch or deciding on where to taste. Jeff handles the flow from one stop to the next.

07-what-guests-remember.webp

what guests remember.

Everybody signs up for a different part of the day. Yet, there is a common thread within our guests' reviews after each tour: the riding is stunning and feels approachable, the food matters, and everyone walks away with a lot of new knowledge to share with their friends and family.

★★★★★

5.0

ON GOOGLE

“

Recommend this tour to anybody who’s interested in seeing and experiencing our rural landscapes in a new way. Definitely works for all levels of riders since they have comfort bikes and E-bikes.

JT

JEN T.

Shifting Gears guest

“

Our tour guide was Amazing. He was knowledgeable, so kind, patient, and teaching us so much overall. We felt so comfortable and even though my husband didn’t have a lot of confidence riding a bike, the E-Bike was so user friendly that you don’t have to be an athlete to do this tour.

MV

MERCEDES V.

Shifting Gears guest

“

It was such a fun way to spend a Sunday. Jeff is so experience-driven. He made sure that every aspect of the day was well planned & made sure everyone had what they needed. The E-bikes were such a blast. The food was DELISH.

KG

KINDRED G.

Shifting Gears guest

08-exploring-with-a-large-group.webp

exploring with a large group?

Private tours open up opportunities for location of choice, tour timing and tour length, depth of experience, and special add-on moments. Shifting Gears has hosted celebrating couples, birthday parties, wedding weekend groups, and corporate outings.

For corporate retreats, sales meetings, and team building events we accommodate teams of 2–13 people, and up to 19 people are possible with one month's notice.

READY WHEN YOU ARE

09-cta-banner.webp

more than a bike tour.

Check out our open public dates and private availability, and choose the experience that sounds right to you.

Move beyond the tour bus. Beyond the classic tasting flights. Move your body. Move your mind. Move your soul.

BEFORE YOU BOOK

Frequently Asked Questions

GET IN TOUCH

let's plan your ride.

Questions about a tour, a private group or a custom day on the bikes? Send us a note and we'll get back to you.

CALL

EMAIL

VISIT

7038 Porters Rd
Esmont, VA 22937

Send us a message

Shifting Gears Travel

Guided bike tours in Charlottesville and Central Virginia. Cycling to wineries, flower farms, oyster growers, and more.

Follow us on:

  • Instagram

TOURS

VISIT & CONTACT

7038 Porters Rd

Esmont, VA 22937

© 2026 Shifting Gears Travel.

Charlottesville & Central Virginia

bottom of page