6 Cycling Events in Tuscany you can’t miss in 2026

A date-by-date guide to Tuscany’s best events, wildest races, and hidden routes, from April to September, perfect for riding through spring and summer.

MAREMMA IN GRAVEL

1–3 May 2026, Marina di Grosseto

The spirit of Maremma in Gravel lies in discovering the wildest and most primordial side of Tuscany, a frontier land that retains a rugged charm far from the classic tourist routes. For a weekend, you will immerse yourself in untamed nature made up of dense forests, marshes populated by wildlife, and solitary cliffs.

The event is divided into two major themed days, starting and finishing in Grosseto:

Far West (Saturday): It heads inland and along the northern coast, passing through Castiglione della Pescaia, Cala Violina, Punta Ala, the Diaccia Botrona Nature Reserve, and the Etruscan Necropolis. You can choose between three routes (long, medium, and short).

Selvaggio Sud (Sunday): Explore the heart of the Maremma Park and the southern coastal areas such as Alberese and Talamone. It is characterized by more scenic passages overlooking the sea and flat dirt roads alternating with hilly stretches.

🚲 Bike type allowed: Gravel bike (recommended), MTB and e-MTB also allowed.

💰 Registration fee:
€35 – 1 day of ride of your choice, includes all refreshments
€70 – 2 days of riding, all meals included
€100 – 2 days of riding, 2 nights at base camp, welcome drink, 2 dinners, all refreshments included

✍️ Registration: https://join.endu.net/login?referer=https%3A%2F%2Fjoin.endu.net%2Ffee&referersrc=&tkn=&token=
Only 150 places available! Registration closes on April 20!

🖥️ Official website: https://www.maremmaingravel.bike

TUSCANY TRAIL

20–26 May 2026, Campiglia Marittima

The Tuscany Trail is the largest international non-competitive bikepacking and gravel event in the world. The route starts from the Etruscan Coast and immerses you in the world-famous icons of Tuscany: from the white roads of Val d’Orcia to the vineyards of Chianti. You will travel through history as you enter Piazza del Campo in Siena, admiring the towers of San Gimignano and the walls of Monteriggioni. An epic journey that combines UNESCO World Heritage villages such as Pienza with the wild nature of the Maremma, among rows of cypress trees and crystal clear sea.

Two route options are available:
Ring Route:
Distance: 430 km, Elevation: 5300 m
On average, the route takes 4 days to complete, but you can take as long as you like.
You will cross dirt roads, vineyards, forests, and historic town centers, with access to private sections reserved exclusively for participants.

Newbie:
Distance: 160 km, Elevation: 1400 m
On average, the route takes two days to complete, but you can take as long as you like.

🚲 Bike type allowed: MTB (recommended). However, over the years, all types of bicycles participated.

💰 Registration fee:
Classic Ticket €99 (4 Dic – 7 Jan), €129 (8 Jan – 31 Jan)
Includes: GPS tracks, maps, race pack with gadgets, bottle of Maremma wine, official cap, etc.
No Stress Ticket €199 (3 Dic – 7 Jan), €229 (8 Jan – 31 Jan)
Includes everything in the Classic package + official T-shirt and other extras provided by the organization.

✍️ Registration link: https://tuscanytrail.it/iscrizioni/
Registration is open until January 31, 2026, or until all available places are filled (limited enrollment).

🖥️ Official website: https://www.tuscanytrail.it

STERRO APPALLA

22-24 May 2026, Valle del Chianti

Sterro Appalla is the “rock” and light-hearted side of gravel: a party on two wheels where fun wins over competition. With Hawaiian shirts and unlikely outfits, the focus shifts from the stopwatch to aperitifs fortified with beer and salami. It is an experience of pure conviviality made up of music, laughter in the dust, and prolonged stops, perfect for those who want to ride “to the max” just for fun.

Route: gravel tracks on dirt roads, winding between Grassina and Greve in Chianti, climbing towards the historic villages of Radda and Volpaia. The route follows the iconic stretches of the Eroica’s white roads, crossing vineyards and villages in Chianti with group rides and various levels of difficulty (Easy, Short, Medium, Long).

🚲 Bike type allowed: The motto of the event is ABAW – All Bikes Are Welcome!

💰 Registration fee: not yet announced

🖥️ Official link: https://www.bbpgravelfirenze.it/sterroappalla/

CICLOSTORICA LA LEOPOLDINA

30 May – 2 June 2026, Follonica

The Ciclostorica La Leopoldina celebrates the charm of vintage cycling. Participants ride along dusty Tuscan dirt roads on historic bicycles, wearing wool jerseys and retro accessories. Every detail, from the steel frames to the refreshment stops offering local products, pays homage to the beauty of the past and the philosophy of slowness. The route winds through the iconic landscapes of the Val di Chiana, passing through villages such as Castiglion Fiorentino and Cortona. You will cycle along the paths of the Leopoldine, surrounded by tree-lined avenues and historic canals.

You can choose 3 routes:
Short: Distance: 29 km Elevation: 130 m
Medium: Distance: 29 km Elevation: 560 m
Long 89 km Distance: 89 km Elevation: 1000 m

🚲 Bike type allowed: vintage bicycles and historic racing bikes

💰 Standard registration fee: €45
Early Bird promotion: €25 for the first 100 people who sign up by the end of January.

✍️ Registration link: https://www.ciclostoricalaleopoldina.it/iscrizione/
Registration openunitl January 31

🖥️ Official website: https://www.ciclostoricalaleopoldina.it

IN GRAVEL

12–13 September 2026 , Magliano in Toscana

In Gravel, it crosses the Maremma region, passing through Magliano, Montemerano, the Abbey of San Bruzio, and the Marsiliana Estate. The route on dirt roads alternates between wild areas and stops for tastings in the Morellino wineries. The event is non-competitive and includes typical refreshments and a final group dinner. It combines the discovery of the territory with local food and wine excellence.

Routes:
Long: Distance: 103 km Elevation: 1450 m Duration: 5-7 hours
Medium: Distance: 78,5 km Elevation: 1350 m Duration: 4-6 hours
Short: Distance: 46 km Elevation: 670 m Duration: 3-4 hours
Social Ride: Distance: 80 km Elevation: 700 m Duration: 4-6 hours

🚲 Bike type allowed: Gravel bike (recommended), also bikepacking or bikes suitable for light off-road riding are welcome.

💰 Registration fee: to be communicated

✍️ Registration link: https://www.ciclostoricalaleopoldina.it/iscrizione/

🖥️ Official link: https://www.ingravel.com

GRINDURO

26 September 2026 – Massa Marittima

AND IF YOU NEED A PLACE TO REST DURING YOUR TRIP, LA PAMPA AWAITS YOU

Welcome to La Pampa Parking Area, a small family-run camp just 10 minutes from the wild beach in Maremma. We are made for nature lovers and free spirits.

👉 Write to us to book on WhatsApp or send us an email at lapampagrosseto@gmail.com
👉 Follow us on Instagram for all the latest news and events in our rest area!