Georgia's Historic Heartland

Bicycle Tour of Athens, UGA, and Madison, GA

An Inn-to-Inn Cycling Tour of Georgia's Rolling Heartland

Athens, GA is home to the University of Georgia and is a cycling hotbed.  Madison, GA has been called "one of the 50 most beautiful small towns in America" by Architectural Digest, and "one of the South's prettiest small towns 2018" by Southern Living.  We have designed this tour to focus on rural  inn-to-inn routes, keeping van shuttles to an absolute minimum.  

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Georgia's Historic Heartland

Athens, GA

Tour Difficulty

Gently Rolling to Moderately Hilly


6 Days, 5 Nights


Hotel Indigo

Nearest Airport

Hartsfield-Jackson Atlanta International (ATL)


From $2710 per person


4/28/24 - 5/3/24 9/29/24 - 10/4/24

Tour Status

Several spots are open on the October date. Availability can change quickly. Please don't make travel plans prior to confirming your spot with us.
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This was a very delightful tour with nice mileage options and great rolling hills. Terrific scenery, wonderful meals. Low pressure tour (no mountains!).
Mary, Boalsburg, PA

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Day 1

5–20 miles, rolling hills

Athens is the quintessential college town, as well as a progressive cycling community.  Well underway is an ambitious plan of paved bike trails, including the North Oconee River Greenway and the Firefly Trail.   Dominated by the University of Georgia campus, Athens has a pleasant, artsy vibe.  Unique local restaurants and shops line Clayton Street, Broad Street and others for block after block.  The UGA campus definitely deserves a visit.  Walk through the famous Arch to see a beautifully landscaped campus with buildings dating back to 1806.  

We'll have bike fittings, orientation and lunch at our upscale hotel in the heart of downtown.  Afterwards we'll enjoy a bike ride in and around town and campus to see a few of the spots that make it unique.  Afterwards we'll enjoy getting to know each other at a private event space downtown.

Day 2

25–51 miles, moderate rolling hills

After breakfast at the hotel you will have the option of commencing today's ride from there, or taking a quick shuttle out of town to start riding in the Georgia countryside.  Today's route will include lovely country and quaint crossroad communities.  One version of this route was named the best route in Georgia a few years ago.

Back in Athens for a second night, you have time to explore downtown and the UGA campus.  We recommend trying a flight at Creature Comforts Brewing Company, a successful local brewery.  Dinner will be on your own this evening, with plenty of options within walking distance of the hotel.  Athens has become a true foodie town, with restaurants such as The National and Last Resort Grill earning an excellent reputation.


Day 3

25–57 miles, moderate rolling hills

We'll ride from downtown Athens to the lovely community of Winterville.  The two communities are now almost entirely connected by the rapidly expanding Firefly Trail.  That launches us onto a wonderful bike ride into the surrounding countryside.  The route over gently rolling terrain will take us across the longest historic covered bridge in Georgia, where we will enjoy a bountiful picnic lunch.  Ultimately we'll pass back through Winterville on our way back to Athens.  Dinner will be as a group tonight at an outstanding restaurant.  

Day 4

35–56 miles, moderate rolling hills

We leave Athens behind today, heading south through a combination of farmland and forest.  You'll get to bike across another historic covered bridge on the way.  Our ultimate destination is the stunningly beautiful town of Madison.  Founded in 1809 as the county seat of Morgan County, it was named for James Madison, who was inaugurated as the 4th U.S. President two months prior.   Saved from destruction during the Civil War by a Union sympathizing mayor, Madison has a remarkably intact and well-maintained inventory of antebellum homes and business structures.  Madison has been called "one of the 50 most beautiful small towns in America" by Architectural Digest, and "one of the South's prettiest small towns" by Southern Living Magazine.  Our lodging for two nights, the James Madison Inn sits across from a town park, and nearby streets are lined with restaurants and boutique shops.

Day 5

23–54 miles, moderate rolling hills

Our layover day in Madison provides multiple cycling route options, so you can choose the distance that appeals to you.  Some of the prettiest scenery of the tour may exist in this area south, east and west of town.  Numerous equestrian estates dot the landscape.  The small former railroad town of Rutledge has a few charming shops and cafes, but mostly the ride will be in rural countryside.

Day 6

25–51 miles, moderate rolling hills

Hotel from My Cousin VinnyOur last day takes us back to Athens.  Yet another day of pleasant cycling on smooth and scenic Georgia roads awaits.  We'll bike through sleepy crossroads communities of Bostwick and Bishop before reaching Watkinsville, just south of Athens.   We'll get you back to your car in time for a late lunch, showers and departure.


$2,710 - $2,810
Single Room Supplement
Bicycle Rental

Low end of tour price range reflects the 6 month Early Bird Discount.  High end of price range reflects no Early Bird Discount. 

Rooms with two beds are only available on nights 1 and 2 of this tour.  Therefore, solo travelers will automatically have private rooms on nights 3 and 4.

What's Included in Your Tour Price


5 nights lodging:  3 at Hotel Indigo and 2 at the James Madison Inn.


Dinner on Nights 1 & 4 All lunches except 1; All breakfasts; snacks; and hors d'oeuvres most nights.

Services of Expert Guides

Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours.  Guides are ready to show you the hidden wonders of each and every destination.

Full Route Support & Luggage Transfer

Service of 1 – 2 support vans on route every day.


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Athens, GA Lodging

Nights 1, 2 & 3

Hotel Indigo, Athens, GA

Hotel Indigo Athens elevates the downtown cityscape with our modern farmstead architectural style. Pairing Southern hospitality with a deep appreciation for local culture, this boutique retreat charms worldly travelers, music aficionados, and trend-setters with its high-end service and chic, art-centric spaces. 

Historic Hotel in Madison, Ga

Nights 4 & 5

The James Madison Inn

Located in historic downtown Madison, The James Madison Inn and Conference Center is within walking distance of antebellum homes, graceful parks, stellar shops, art & antique galleries, spas and fine restaurants. It is elegantly appointed and offers a unique, luxurious way to experience Madison. Seventeen rooms and two suites in this boutique hotel set the stage for luxurious Southern hospitality. With paintings of landmarks, custom furniture and peerless service, the inn brings local lore and Southern charm to life for guests.



The terrain is rolling hills.   This generally equates to 1,500 - 2,000 feet of climbing on a 30-40 mile route.  Mileage each day will range from 25 – 55+ miles, with multiple options available.  As with all Carolina Tailwinds tours, you can take advantage of the support van to "leap frog" ahead on the route.

All of the routes are on country back roads or busier roads with bicycle accommodation, and the scenery is beautiful, including well-maintained farms, equestrian estates, and forest.

Tour Point of Origin:

Hotel Indigo, 500 College Ave, Athens, GA  30601

Getting to the Tour Start (Athens, GA)

Driving: Approximate travel distance to Athens--

  • Atlanta, GA:  72 miles
  • Augusta, GA: 94 miles
  • Savannah, GA: 219 miles
  • Greenville, SC: 94 miles
  • Jacksonville, FL:  341 miles

Airports: Hartsfield-Jackson Atlanta International Airport (ATL)
Service by all major airlines (75 miles from tour start/end location).

Greenville Spartanburg International Airport  (GSP)
Service by Allegient, American, Delta, Southwest & United (105 miles from the tour start).

Ground Transit: Groome Transportation offers a shuttle between ATL to Athens that makes 10 round trips daily.  Reserve online at or call:  (706) 612-1155. 
Rental cars, Uber, and limos are available at Atlanta (ATL) and Greenville (GSP).

Parking:  We have arranged for complimentary long term parking for the duration of your tour in Athens.  

Arrival/Departure Timing

In order to participate in the Day 1 meeting and bike ride, please plan to arrive in Athens no later than 11:30 a.m. (10:30 a.m. if renting a bike).

 On Day 6, we will return to Athens between 12 and 1:00 pm.  Flight timing on our last day should not be booked any earlier than 5:00 p.m. from Atlanta. 

Extend Your Vacation

Before or after our activity packed tour, you may want to tack on a few days. 

Athens:  This vibrant college town has plenty to explore.   

  • The State Botanical Garden of Georgia is just south of town and boasts 313-acres of themed display gardens, including the Flower Garden, the International Garden, the Heritage Garden, the Shade Garden, and 5 miles of nature trails.

Note:  Athens is home to the 92,700 seat Sanford Stadium, home to the 2021 National Champion Georgia Bulldogs Football Team.  On home football game weekends, lodging is scarce or non-existant and extremely expensive.  On those weekends, you may want to choose lodging near the Atlanta airport if flying, or in another community in the region if driving.

Bulldogs schedule:

Atlanta, GA:

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