-->
www.challenging.events

Hampshire Hilly Hundred

calendar_today 16 May, 2027

directions_bike Cycling

sell £33.00 – £39.00

Hampshire Hilly Hundred

About the Event

Hampshire Hilly Hundred Sportive
Experience the ultimate cycling challenge as you pedal through the rolling hills and picturesque landscapes of Hampshire on May 16, 2027. The event starts at Sparsholt College in Winchester and offers two distances: a grueling 102-mile route packed with steep climbs and exhilarating descents, or a more manageable 68-mile option for those looking to test their limits without overextending themselves.
The longer course features some of Hampshire's most iconic hill climbs, including Beacon Hill, Watership Down, and Windmill Hill. Each ascent offers breathtaking views across the undulating countryside, while the descent rewards you with thrilling speed and a sense of accomplishment after conquering each summit. With an elevation gain exceeding 6000 feet, this route is not for the faint-hearted but promises to be one of the most rewarding sportives on your calendar.
Throughout both routes, participants are supported by fully signed directions and well-placed marshals who ensure safety at every turn. Feed stations along the way provide essential nutrition and hydration, allowing you to focus solely on enjoying the ride without worrying about logistics. Mechanical support is also available should any unforeseen issues arise during the event.
Upon crossing the finish line back at Sparsholt College, riders are greeted with a medal, refreshments, snacks, and chipped timing results. Those who prefer not to collect a medal can opt out of this service as well. The atmosphere on race day is electric, filled with camaraderie among fellow cyclists and encouragement from spectators.
Previous participants have praised the event for its impeccable organization, friendly community spirit, and scenic beauty. Whether you're aiming to push your physical boundaries or simply enjoy an adventurous ride through stunning countryside, the Hampshire Hilly Hundred Sportive promises a memorable day out on two wheels.
Registration opens at 07:00 with start times scheduled between 07:30 and 09:00 for both distances. The event concludes by 16:30. Don't miss this opportunity to join one of the most beloved cycling events in Hampshire, which has sold out in previous years.
For those interested in helping behind the scenes, there's a special offer allowing you to ride for free if you assist with registration or car parking duties on race day. Just sign up using the provided form and indicate your willingness to volunteer.
Remember to review our Code of Conduct before attending to ensure everyone can enjoy this fantastic event while fostering an inclusive and respectful environment.
Join us in Winchester as we celebrate cycling in all its challenging glory!

Races Offered

68 miles

May 16, 2027

straighten

Distance — 109.4K

terrain

Type — Cycling

timer

256 days remaining

sell

£36.00

NO MEDAL 68 miles

May 16, 2027

straighten

Distance — 109.4K

terrain

Type — Cycling

timer

256 days remaining

sell

£33.00

NO MEDAL The Hundred

May 16, 2027

straighten

Distance — NO MEDAL The Hundred

terrain

Type — Cycling

timer

256 days remaining

sell

£36.00

The Hundred

May 16, 2027

straighten

Distance — The Hundred

terrain

Type — Cycling

timer

256 days remaining

sell

£39.00

Weather History

These values represent the 3-year monthly averages for May in Hampshire.

thermostat Temperature
8.9° / 17.6°
wb_sunny Feels like
6.1° / 14.8°
light_mode Avg sunshine hours
11h 6m
water_drop Avg rainfall
1.9 mm
ac_unit Avg snowfall
air Avg wind speed
12.9 km/h (Gentle breeze)
opacity Sweat loss rate
Low
terrain Course conditions
Firm and slightly soft
sunny Max UV Index
Moderate (4.2)
humidity_mid Humidity
76.0%
wb_twilight Sunrise
05:15
nightlight Sunset
20:49

About Hampshire

Learn more about the host city, Hampshire.

Scenic view of

Stretching from Solent beaches in the south west, to London's suburban fringe in the north-east, Hampshire is the largest county in South East England. Known as Jane Austen's County after its most famous daughter, Hampshire has a wealth of attractions to offer the traveller. Visitors may see one of England's greatest cathedrals in Winchester, ascend to the top of the South's tallest landmark in Portsmouth or fish for trout in crystal clear chalk rivers.

Read more launch

Hotels & Places to Stay

Runner Reviews

Read what other athletes have to say about their experience at the Hampshire Hilly Hundred.

No reviews yet

Be the first to share your experience with the community!

Suggest an edit

Spotted an error or missing detail about the Hampshire Hilly Hundred? Help us improve.

Nearby Races

Explore other exciting events happening in this same region.

Andover Trail Marathon.

Andover Trail Marathon.

location_on Andover, South East, GB

calendar_today Sep 05, 2026

Maggie's Southampton Hats Off Swim

Maggie's Southampton Hats Off Swim

location_on Southampton, South East, GB

calendar_today Sep 06, 2026

Run The Down - Free Trail Event

Run The Down - Free Trail Event

location_on Dummer, South East, GB

calendar_today Sep 06, 2026

New Forest Marathon and Half Marathon

New Forest Marathon and Half Marathon

location_on Brockenhurst, South East, GB

calendar_today Sep 13, 2026

Recommended for You

Hand-picked events we think you’ll love.

Gravel 100 - 4 September - Individual Registration

Sep 03, 2026

Gravel 100 - 4 September - Individual Registration

The Anglian Water WaterAid Cycle Ride is back! Join us in supporting WaterAid’s vision of making clean water, decent to…

Read more
SAS ENDURANCE - September 2026

Sep 04, 2026

SAS ENDURANCE - September 2026

SAS ENDURANCE The toughest SAS Test Week Route March. 64km over the highest peaks in South Wales. Please note: NEW TICK…

Read more
Challenge Almere-Amsterdam 2026

Sep 09, 2026

Challenge Almere-Amsterdam 2026

The oldest long distance race in Europe, the second oldest in the World. Be part of history and race this Classic Long …

Read more
KIDS - Kids

Apr 10, 2027

KIDS - Kids

l y a des courses où l’on vient pour faire un chrono. Et puis il y a L’Hourcancilloise. Un événement où tu arrives avec…

Read more

Get race deals & updates

Subscribe to our newsletter for curated race picks and discounts.