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Experience a captivating blend of scenic vineyards, coastline, and cultural heritage on a self-guided bike tour through southern England.
Riding through the rolling hills of Sussex in beautiful South East England offers a truly unique experience, with vibrant green countryside, charming villages, and a picturesque coastline that has long been a gateway to history. On this self-guided bike tour in Britain, starting from a handpicked hotel just outside London, you’ll meander through peaceful lanes, discovering historic stone cottages, cobbled streets, and cozy pubs. Explore the sun-soaked vineyards of the South Downs, where the chalky soil rivals that of France’s Champagne region, and indulge in award-winning local sparkling wine. There’s no landscape quite like the English countryside, and no cycling adventure quite like this, where you’re free to explore at your own pace. Learn more about Self-Guided trips and if they're right for you »
Trip Wows
Discover the sun-soaked vineyards in the South Downs and sample England's award-winning sparkling wines
Enjoy a traditional treat of "fish and chips" on the pebble beach of the vibrant seaside resort town of Brighton
Pamper yourself at the hotel's beautiful spa set in an Elizabethan Manor House
Explore the charming village of Lewes, home to one of the oldest breweries in the UK
Enjoy unrivalled cycling down beautiful lanes, through quaint villages, and surrounded by a landscape rich in history
Colorful row houses in Brighton
Brighton Beach
Brighton is a vibrant seaside city on England’s south coast, known for its iconic pebble beach, lively arts scene, and historic pier.
What Guests are Saying
A very well-conceived trip with fun routes, excellent food, and interesting side tours. We felt Trek was fully behind us whilst enjoying the freedom of self-guidance. And the Trek bikes inspired confidence!
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Every day was a great experience that really surpassed my expectations. The attention to detail was amazing with surprises at every turn.
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Great Ride
The Vineyard Loop
Our flagship ride, wind your way along quiet country lanes and stop off at leading local vineyards en route!
Dates & Pricing
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Itinerary
Day-to-Day
View full itineraryWhere to Arrive
Airport:
Gatwick Airport (LGW)
Pick-up location:
Ockenden Manor Hotel, Cuckfield, England
Pick-up time:
11:00 AM
Where to Depart
Airport:
Gatwick Airport (LGW)
Drop-off location:
Ockenden Manor Hotel, Cuckfield, England
Drop-off time:
11:00 AM
Additional Arrival Information
We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into London Gatwick Airport (LGW).
London Gatwick has a train station in the south terminal with direct trains to Haywards Heath station about every 10 minutes, with a journey time of 15 minutes. One way tickets are between £7 and £15 (approximately $8-18 USD) depending on time of travel. Direct trains are also available from several London stations including London Victoria, Kings Cross, London Bridge and St Pancras. Journey time from London station is between 30-50 minutes. One way tickets between London Terminals (all London stations) and Haywards Heath are between £15 and £30 (approximately $18-36 USD) depending on time of travel. From Haywards Heath station, a short taxi ride (10 minutes) is the easiest way to reach the hotel. There is a taxi stand outside the ticket hall. Taxi cost is about £30 (approximately $36 USD).
An airport transfer from LGW to the hotel in Cuckfield is another easy option. It’s a 30 minute journey and costs around £40 (approximately $48 USD) each way. Tickets can be purchased at Gatwick Taxi's.
Your Trek Travel host will meet you at your trip hotel Ockenden Manor (Ockenden Lane, Cuckfield , West Sussex, RH17 5LD) at 11:00 AM on the first day of the trip. Depending on the number of guests booked for your departure date, it is possible we will ask you to shift your meeting time by approximately 30 minutes. Please have your riding gear readily accessible to avoid having to unpack your luggage. After a trip overview, you may change into your cycling gear where you will then be fitted to your Trek bike ensuring you will be comfortable for the week. Following a safety talk and a few tips about cycling in the area you will set off at your own pace through the roads of Sussex.
If you will be late for the meeting or are going to miss it altogether, please inform your host. If you cannot reach them, please call our hotel, Ockenden Manor (+44 (0) 1444 416111) and leave a message with your expected arrival time and contact details.
Additional Departure Information
Your Trek Travel host will meet you at 11:00 AM at the trip hotel to take your bike and equipment and say farewell before your departure.
Welcome to Cuckfield, one of the prettiest villages in West Sussex
Overview
Meet your Trek Travel host at 11:00 AM in the hotel lobby in picturesque Cuckfield, a charming village that time forgot, tucked away in the beautiful Sussex countryside. After familiarizing you with your upcoming itinerary, your host will spend some time discussing safety, the rules of the road, and fitting you to your Trek bike to ensure the best fit and comfort for the week. Afterward, you are free to spend the day as you like—head straight to the fabulous hotel... Meet your Trek Travel host at 11:00 AM in the hotel lobby in picturesque Cuckfield, a charming village that time forgot, tucked away in the beautiful Sussex countryside. After familiarizing you with your upcoming itinerary, your host will spend some time discussing safety, the rules of the road, and fitting you to your Trek bike to ensure the best fit and comfort for the week. Afterward, you are free to spend the day as you like—head straight to the fabulous hotel spa or take your bike out for a short spin. Today's route will loop you through town and onto country lanes to Nymans garden, a local National Trust property from the 1800s. It is a great way to ease into riding, finding your own pace while getting acquainted with your Trek bike. This evening, make use of our personalized recommendations as you decide which local restaurant to try first. Read More
Hotel
Hotel Ockenden Manor
Meals included
Breakfast
Highlight of the Day
Historical Nymans garden
Ride to the Nymans garden, a beautiful, local National Trust property from the 1800s.
Ride Options
Ride Option 1
TODAY'S RIDE:
Cuckfield to Nymans Gardens Loop - Approximately 15 miles | 24 km and 876 feet | 267 m
Ride Option 2
SHORT OPTION:
Cuckfield to Bolney Wine Estate - Approximately 11 miles | 18 km and 618 feet | 188 m
Ride Option 3
AVID OPTION:
Cuckfield to Twineham to Wineham to Nymans Gardens Loop - Approximately 20 miles | 32 km and 1,307 feet | 398 m
Explore the heart of rural Sussex—the beautiful county town of Lewes
Overview
Following a bountiful breakfast, head out through quiet residential streets before branching out onto lovely country lanes toward the picturesque village of Lindfield. The route takes you past Sheffield Park, not only home to a famed country house and gardens, but also the Bluebell Steam Railway. You'll follow a quiet route south to the town of Lewes—once the home of Thomas Paine (try the Tom Paine Ale from the local brewery!). Lewes sits in the Ouse Valley with t... Following a bountiful breakfast, head out through quiet residential streets before branching out onto lovely country lanes toward the picturesque village of Lindfield. The route takes you past Sheffield Park, not only home to a famed country house and gardens, but also the Bluebell Steam Railway. You'll follow a quiet route south to the town of Lewes—once the home of Thomas Paine (try the Tom Paine Ale from the local brewery!). Lewes sits in the Ouse Valley with the chalk hills of the South Downs surrounding it and providing some great scenery. It’s home to a wide range of cafes, restaurants, and antique shops, but the jewel in the crown is its Norman castle. It played a role in the formation of British democracy and is well worth a visit. The ride back to the hotel passes along some scenic roads before you pick up your tire tracks at Lindfield and sneak through the hidden roads of Haywards Heath. Tonight, treat yourself to another meal of your choice in town. The recommendations are at your fingertips. Read More
Hotel
Hotel Ockenden Manor
Meals included
Breakfast
Highlight of the Day
Discover the town of Lewes
Lewes is home to a wide range of cafes, restaurants, and antique shops and don't miss its historic Norman castle!
Ride Options
Ride Option 1
TODAY'S RIDE:
Cuckfield to Lewes Loop - Approximately 40 miles | 65 km and 2,310 feet | 704 m
Ride Option 2
SHORT OPTION:
Cuckfield to Lewes Return - Approximately 32 miles | 52 km and 1,755 feet | 535 m
Ride Option 3
AVID OPTION:
Cuckfield to Glynde to Lewes Loop - Approximately 44 miles | 72 km and 2,564 feet | 782 m
Pedal through the vineyards and discover some of England’s finest sparkling and white wines
Overview
Today’s loop ride takes you south to the foot of the South Downs, which is the heartland of English winemaking. The region’s finer climate, proximity to the sea, and geology of the area make this the perfect setting for cultivating delicious and award-winning wines, and today you’ll have the chance to visit some of the area's most prestigious vineyards. After a stretch on the wonderfully named Slugwash Lane, you’ll head towards Ditchling Common, the home of ... Today’s loop ride takes you south to the foot of the South Downs, which is the heartland of English winemaking. The region’s finer climate, proximity to the sea, and geology of the area make this the perfect setting for cultivating delicious and award-winning wines, and today you’ll have the chance to visit some of the area's most prestigious vineyards. After a stretch on the wonderfully named Slugwash Lane, you’ll head towards Ditchling Common, the home of Ridgeview wine estate - a wine producer that has not only won global awards for its Sussex Sparkling but has been served by the Queen to prestigious guests including President Obama over recent years. After a visit, you’ll continue on to the village of Ditchling where The Bull provides a very tempting pub option for a mid-ride refuel. The route picks up Underhill Lane here, following the curvature of the South Downs, before turning north towards Bolney and another fabulous winery. This makes for a great final stop as there are just a few more miles to the hotel from here. In the afternoon take some time to relax before enjoying dinner at your leisure at a restaurant in town that best suits your taste. Read More
Hotel
Hotel Ockenden Manor
Meals included
Breakfast
Highlight of the Day
Ridgeview Wine Estate
Visit Ditchling Common, the home of Ridgeview wine estate. Their wine has not only won global awards for its Sussex Sparkling but has been s... Visit Ditchling Common, the home of Ridgeview wine estate. Their wine has not only won global awards for its Sussex Sparkling but has been served by the Queen to guests including President Obama! Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Cuckfield to Ditchling to Westmeston Loop - Approximately 31 miles | 49 km and 1,379 feet | 420 m
Ride Option 2
SHORT OPTION:
Cuckfield to Ditchling Loop - Approximately 27 miles | 44 km and 1,210 feet | 369 m
Ride Option 3
AVID OPTION:
Cuckfield to Ditchling Loop (with Jack and Jill Windmills Climb) - Approximately 34 miles | 55 km and 2,128 feet | 649 m
Cycle to Brighton Beach, a real British seaside treasure
Overview
Get ready for a fantastic day of cycling that takes you on the Downs Link Trail, a traffic-free path that follows an abandoned railway line that runs all the way to the coast. Along the way, you’ll pass the ruins of Bramber Castle before following the river Adur to the coast at Shoreham. From here you'll follow the promenade into the heart of the bustling city of Brighton & Hove, one of the south coast's coolest destinations. Here you have the choice of going trad... Get ready for a fantastic day of cycling that takes you on the Downs Link Trail, a traffic-free path that follows an abandoned railway line that runs all the way to the coast. Along the way, you’ll pass the ruins of Bramber Castle before following the river Adur to the coast at Shoreham. From here you'll follow the promenade into the heart of the bustling city of Brighton & Hove, one of the south coast's coolest destinations. Here you have the choice of going traditional with fish and chips on the beach or going contemporary with a host of trendy eateries and boutiques dotted along the quaint North Laines streets. Your route finishes at the train station, where you can hop on for a 15-minute ride back to Haywards Heath before cycling the remaining couple of miles back to the hotel. Tonight, take a relaxed stroll in town and find a restaurant of your choice. Raise a glass and toast to an incredible self-guided bike tour in southeastern England, riding off the beaten track and discovering a land of beauty, culture, and excitement. Read More
Hotel
Hotel Ockenden Manor
Meals included
Breakfast
Highlight of the Day
Traditional Fish & Chips at Brighton Beach
Tuck into some traditional fish and chips on the beach or go for a contemporary alternative and experience a real British day by the seaside... Tuck into some traditional fish and chips on the beach or go for a contemporary alternative and experience a real British day by the seaside! Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Cuckfield to Brighton (with train back) - Approximately 30 miles | 47 km and 987 feet | 301 m
Ride Option 2
SHORT OPTION:
Cuckfield to Shoreham (with train back) - Approximately 22 miles | 35 km and 713 feet | 217 m
Ride Option 3
AVID OPTION:
Cuckfield to Brighton Loop - Approximately 48 miles | 77 km and 2,186 feet | 666 m
Activities
Activity 1
Train ride after your bike ride
Take a 15-minute train ride from Brighton back to Haywards Heath
Rise early for a farewell morning loop
Overview
On this final day of your self-guided bike tour in Sussex, take the morning to sleep in and relax, savoring a long breakfast, or choose to have a final spin before leaving Cuckfield. You’ll have enough time to return back to the hotel, shower, and change before you depart. Your Trek Travel host will meet you at 11:00 AM at the hotel to take your bike and say farewell, concluding your self-guided journey.
Meals included
Breakfast
Highlight of the Day
A final spin through the English countryside
There's no better way to say farewell to your South England Self-Guided Bike Tour than a sunrise ride.
Ride Options
Ride Option 1
TODAY'S RIDE:
Cuckfield to Ardingly Loop - Approximately 12 miles | 20 km and 1,115 feet | 340 m
View full itinerary to print.
View full itineraryActivity Information
There are a variety of non-riding options on this trip for riders who want to take the afternoon off or travel companions who want to spend little or no time in the saddle. Non-riders are welcome on a Self-Guided trip if they are staying in the same room with a riding guest. Non-riders will be offered a $500 discount from the trip price. Please contact a trip consultant for details and to book a non-riding companion. Some of these options may need to be scheduled before your trip—please contact one of our Trip Consultants for more information. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options on this trip are:
- Sussex is the home of the British winemaking scene: enjoy a wine tasting in some of its amazing wineries
- Visit Brighton, a vibrant, bohemian city rich in culture and history
- Enjoy some lovely walks with spectacular views of the coastline and the Weald on a long distance trail along the ridge of hills known as the South Downs
- Explore Nymans garden
- Experience the grandiose gardens, amazing artefacts, and iconic architecture offered by the old country houses and estates, many of which are owned by the National Trust and open to the public
- Visit the Weald & Downland Living Museum and the Arundel Castle
- Enjoy a visit of Knepp Estate, a farm that has become famous for its pioneering rewilding work
- Visit the Fishbourne Palace, the largest Roman Villa north of the Alps
On a self-guided tour you need to feel comfortable changing a flat, as this is a common event when cycling. All self-guided trips include Ride With GPS, an app which is like having a personal guide in your pocket! You'll get turn-by-turn directions and navigation along with local recommendations. In the rare case of a bicycle breakdown or mechanical issue beyond a simple repair, your Ride With GPS app will have your full itinerary with detailed contact information with emergency phone numbers to call for assistance. Learn more about our Self-Guided Bike Tours.
- Ride With GPS app loaded with up to three daily route options
- Turn-by-turn directions and recommendations pinned on a map
- Emergency phone numbers and local highlights
Hotels
Cuckfield, England
Ockenden Manor Hotel & Spa
LuxuryA fine and tranquil Elizabethan Manor House with lavishly decorated rooms, an outstanding modern spa, a delightful swimming pool, and an award-winning restaurant set on eight acres of beautiful grounds overlooking Cuckfield Park. With its history and character, this elegant property is a wonderful place to both unwind and indulge while enjoying stunning views all around.
... Learn moreBikes & Gear
Ride the Best Bikes in the Industry
Road
E-Bike
Road
Trek Checkpoint ALR 5 2022
It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. The Checkpoint ALR 5 is a high-quality build that is light and fast, and is incredibly comfortable for many miles of exploring beautiful terrain. What sets this model apart is the performance components, progressive geometry, and a wealth of features that give you a smooth ride even when the pavement is a bit more rugged. It is the ideal choice for your kind of adventure.
E-Bike
Trek Electric-Assist Verve+ 1
With its Low-Step frame design, hopping on and off the Trek Verve+ is super easy. The suspension seat post will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear.
Additional Gear
- Trek Travel water bottle to keep
- Universal phone case and mount along with portable battery backup
- RWGPS Experience App with pre-loaded routes and itinerary
- Bontrager front and rear Flare R lights
- A flat pack containing a tube, levers, and a CO2 cartridge with inflator
- Choice of Shimano SPD-SL road style pedals, Shimano SPD mountain style pedals, caged, or flat pedals
- Bontrager helmet
- Bontrager saddle
- For the most comfortable ride, we recommend you bring your own saddle. If you prefer, you can bring your own pedals and helmet on the trip and your host will install your gear on the first day during your bike fit.
Trip Inclusions
- Four nights of accommodation at one handpicked hotel
- Daily breakfast
- Daily lunch and dinner recommendations
- Trek Travel water bottle
- Up to three daily route options on riding days
- A bike lock, all necessary chargers and a floor pump
- Bike fit on the first day to help you find your optimal riding position
- Ride with GPS Experience on your phone for turn-by-turn directions and daily itinerary information. A universal phone case and portable battery will be provided for on-bike navigation
Additional Details
Your Day. You Decide.
Our self-guided vacations are designed to fit all types of travel styles. Whether you like to spend your time relaxing or on a non-stop adventure, you get to decide what your day looks like. Choose your mileage, itinerary, and experience level and leave the rest to us!
Your Trip Need to Knows:
- Starting January 8th, 2025, travelers entering the United Kingdom will need an Electronic Travel Authorization (ETA). This digital permission, costing £10, allows multiple journeys and is valid for two years or until your passport expires. Approval typically takes about 3 days, so it’s best to apply early. Note that dual citizens do not need an ETA, but it is required even for layovers. Apply via the UK ETA app or online at www.gov.uk.
- We do our best to avoid busy roadways as much as possible, however, urban riding and sections of busy roads are unavoidable for some segments of your rides.
- There are some short sections of gravel and uneven lanes on this bike tour which can be slightly bumpy at time however our Trek Checkpoints and Verve’s are fitted with wide, semi-slick tires that are perfect for this terrain.
- We recommend that you bring good walking shoes or boots as there are some fantastic hikes nearby including the South Downs Way — a long distance trail along the ridge of hills known as the South Downs – and some lovely walks with spectacular views of the coastline and the Weald.
- Look right, ride left! In England, cyclists follow traffic on the left side of the road. If this differs from what you’re used to, don’t worry—your guides will remind you along the way. Take extra care when riding, crossing intersections, and navigating roundabouts.
Before and After Your Trip
London, England
London, a city with a history of nearly two millennia, is a cosmopolitan hub and Britain's economic, cultural, and transportation center. The City of London, its historic core, founded by the Romans, and the City of Westminster, the seat of the national government, are key areas. London's cultural diversity is mirrored in over 300 languages and top academic institutions. Major attractions include the British Museum, National Gallery, and West End theatres. The city boasts four World Heritage Sites: the Tower of London, Kew Gardens, and the historic Greenwich. Adding to its charm is an amazing restaurant scene, offering a vast array of global cuisines, and a vibrant cultural tapestry that includes numerous music, art, and cultural festivals. We recommend the following accommodations for your pre- and post-trip hotel:
Where to Stay
The Henrietta
This 4-star boutique hotel is located in the heart of Covent Garden and a short walk from Covent Garden Underground on the Piccadilly line, and within walking distance of Soho, The Strand, and Leicester Square. www.henriettahotel.com
The Clermont
Just steps from Trafalgar Square and Covent Garden, The Clermont, Charing Cross is housed in a beautiful, Grade II-listed building next to Charing Cross train station. This 4-star hotel features a restaurant and stylish rooms. www.theclermont.com
The Hoxton
Situated in the heart of London, this 4-star hotel offers contemporary accommodation which boasts roaring fires and exposed brick work. Old Street Tube Station is only five minutes’ walk away, providing easy access to London’s main attractions, and it is also known for its fabulous breakfasts. www.thehoxton.com
Weather
Average monthly temperature and precipitation
| Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| High | 46.0°F· 7.8°C | 47.0°F· 8.3°C | 52.0°F· 11.1°C | 56.0°F· 13.3°C | 63.0°F· 17.2°C | 68.0°F· 20.0°C | 72.0°F· 22.2°C | 71.0°F· 21.7°C | 66.0°F· 18.9°C | 59.0°F· 15.0°C | 52.0°F· 11.1°C | 47.0°F· 8.3°C |
| Low | 36.0°F· 2.2°C | 35.0°F· 1.7°C | 37.0°F· 2.8°C | 40.0°F· 4.4°C | 46.0°F· 7.8°C | 51.0°F· 10.6°C | 55.0°F· 12.8°C | 54.0°F· 12.2°C | 49.0°F· 9.4°C | 45.0°F· 7.2°C | 39.0°F· 3.9°C | 36.0°F· 2.2°C |
| Rain | 1.86"· 4.72 cm | 1.27"· 3.23 cm | 1.01"· 2.57 cm | 1.23"· 3.12 cm | 1.02"· 2.59 cm | 0.91"· 2.31 cm | 1"· 2.54 cm | 0.93"· 2.36 cm | 0.93"· 2.36 cm | 1.85"· 4.70 cm | 1.62"· 4.11 cm | 1.7"· 4.32 cm |
FAQs
The best time to visit Sussex, in southeastern England, is late-June through September. In this period you have pleasant temperatures with temperatures that range from 68-77°F (20-25°C) and little precipitation. Always remember that rain is possible at any time, weather in the UK can be unpredictable! Please, be prepared with the proper rain gear in order to best enjoy your vacation.
View our Packing List
To reserve your space on a trip, you can either call us at 866-464-8735 to speak with an expert Trip Consultant or book online any time by clicking the “BOOK THIS TRIP” icon near the upper right of each destination’s overview page.* Once you have submitted your reservation online, a Trip Consultant will contact you within one business day to answer any questions you may have and to confirm space, bike, and room availability on your desired trip. Your booking will be finalized once your no-risk deposit is paid. If you make a reservation more than 90 days prior to the trip, a $750 no risk deposit is due at the time of booking.** If you reserve your trip less than 90 days prior to the departure, the full balance is due at the time of booking. Once your booking is complete you will receive an email confirmation with important information pertaining to your trip.
*Please note that select trips cannot be booked online at this time. For those trips, please call a trip consultant at 866-464-8735.
**Deposit amounts vary for all Race, Cross Country, Special Edition, Ride Camp, Discover, and Self-Guided tours. Please confirm deposit amounts for all trips with your Trip Consultant at time of booking.
When a trip is booked, a guest confirmation letter is immediately sent out. One week prior to the trip start, you’ll receive an email containing your trip start meeting location reminder and any last-minute information that you’ll need to know before you go. Once you arrive at your destination, your Trek Travel host will brief you on the day-to-day plan for the trip and give you an overview on the daily route information and detailed maps within the Ride with GPS app. The turn-by-turn directions allow you to ride with complete confidence and independence.
We understand things happen in life and sometimes you have to cancel or change your tour.
Read our Cancellation Policy
Our Trip Consultants are available to assist and can answer your questions. Please call us at 866-464-8735.
Trek Travel recommends that you purchase a travel protection plan to help safeguard you and your travel investment against the unexpected. We offer a travel protection plan through Arch RoamRight that provides coverage for unforeseen events that could affect your ability to travel with us. Learn more about our Travel Protection
We've collaborated with a specialized travel agency committed to delivering tailored vacation planning, ensuring your entire Trek Travel journey is nothing short of unforgettable. Learn more about our Travel Services
Your Self-Guided trip price is per person based on two guests sharing a room. If you are a solo traveler or if you want to stay in your own private room while traveling with other people, you will have a Single Supplement Fee added to your trip price at the time of booking.
Didn't find what you were looking for? Check out our General FAQs section. You will find answers to the most common questions that don't necessarily pertain to a specific trip. See Self-Guided FAQs
