With its excellent road and rail connections getting to Carlisle is easy. We aim to leave Carlisle by no later than 14:30 today for the transfer to Kirkcudbright, in Dumfries and Galloway (approximately 2 hours) where we will spend the night. For those arriving by car, you will be able to leave your vehicle in Carlisle for the duration of the trip.

Situated on the tidal River Dee, Kirkcudbright provides one of the best natural harbours on the Galloway coast and is a friendly little place. It is dominated by the impressive MacLellan’s Castle which was built in the 1570s and still remains a focal point of the town.

Once here, there will be an opportunity to properly meet your fellow coast to coasters. Our evening meal will be taken together, during which our guide team will talk everyone through what to expect over the next few days.

• Meals: Breakfast, lunch
• Ascent: 1,045 Metres Approx.

After an early breakfast we make our way by minibus to Stranraer, the gateway to the Rhins of Galloway. Situated beside Loch Ryan on the west coast of South Scotland Stranraer marks the start of our ride.

Within a few lochside pedal strokes we’ll be away from the town and heading along some quiet country lanes and our cycling journey underway. Our first treat is after only just a few miles when the Galloway coastline appears near Stairhaven. Soon afterwards we reach the gorgeous Auchenmalg Bay with its expanse of stunning sandy beach.

Heading inland across the Machars peninsula narrow lanes lead us to Wigtown, Scotland’s National Book Town. It’s a bit early for a tour of Bladnoch, Scotland’s most southerly distillery but certainly the perfect time for a coffee kick. The next major stop is at the small market town Newton Stewart (on the banks of the River Cree) and is here we take lunch. Our afternoon cycling then crisscrosses along and takes in Creetown before heading inland to the lovely Gatehouse of Fleet. Our final few miles take us back along the Galloway Coast to Kirkcudbright. Our accommodation is as the previous night with the evening meal taken once more in Kirkcudbright.

• Meals: Breakfast, lunch
• Ascent: 1,260 Metres Approx.

We leave the coast behind today and continue our journey inland from Kirkcudbright. Our morning ride is a mostly flat stretch with some undulating sections, with a quick pit-stop planned at Castle Douglas after around 10 miles. From here terrain remains much the same before we pick up a series of dedicated cycle paths to navigate our way through Dumfries. The town was home to Robert Burns, Scotland’s National Bard who lived in the town in the 1790s and more recently Peter Pan author J M Barrie.

Continuing eastwards, Lockerbie not only is our lunch-stop but a point at which the landscape starts to change, and we start to climb up into the hills. The scenery throughout this afternoon’s ride is simply breathtaking and all the ups and downs are rewarded with fantastic views. Our route is well surfaced for the main part and takes us past Hart Fell, Bombie Hill and then skirts Castle O’er Forest before descending to the ‘Muckle Toon’ of Langholm. It’s a small place rich in stories and traditions. Come summer, Common Riding (a centuries old equestrian tradition) is an unforgettable spectacle, and nearby Gilnockie Tower boast relations to the first man on the moon, Neil Armstrong.

• Meals: Breakfast, lunch
• Ascent: 1,100 Metres Approx.

Heading up from the River Esk you’ll be soon honing your gear selection for the most challenging day of the trip. It all starts with the ‘cheeky climb’ of Whita Hill from the get-go, where a couple of sharp hairpins will focus your attention. Near the top and perfect for taking a breather, as well worthy of a photo is the memorial dedicated to poet Hugh MacDiarmid who was born in Langholm. A little higher on the moorland you’ll also see a monument to Sir John Malcolm, one of the four knights of Eskdale.

This section is a great place for birdwatching and you might even be lucky enough to spy a rare Golden Eagle soaring high above, or some of the feral goats that have made the moors their home.

The descent from the highest point of your C2C makes all the uphill efforts well worth it. Sooner than you know it you’ll reach Newcastleton where a morning cappuccino is certainly on the cards! Caffeinated-up our route continues past Hermitage Castle and Shankend Viaduct before reaching Hawich.

Situated on the River Teviot the town is internationally famous for its fine quality knitwear and home to the lovely Wilton Lodge Park where we take lunch.

Our final miles roll nicely through some small villages and lovely open countryside as we head to Selkirk where we end a memorable day on the bike.

• Meals: Breakfast, lunch
• Ascent: 825 Metres Approx.

A much easier, rolling day is in store for us, pretty much following the River Tweed for the duration of the ride. Our first port of call (a few miles in) is at Melrose. Situated next to the Eildon Hills and famous for its ruined castle and the Rugby Sevens, it’s a picturesque town. From Melrose, it is a short ride to then cross the River Tweed at Dryburgh before we take the quiet farming lanes to reach Kelso. It’s here we’ve our lunch-stop planned close to the town centre.

Our route then sees us cycling past Coldstream (home of the Coldstream Guards), close to the border with England. Further along, the route dips briefly into the English county of Northumberland before recrossing into Scotland over the Union Chain Bridge.

Spanning the River Tweed between Horncliffe in England and Fishwick in Scotland, it was the longest wrought iron suspension bridge in the world upon its opening in 1820. Things were a bit smaller back then and as it is a narrow bridge, we’ll need to say goodbye to our support vehicle for this section.

Our final stretch takes us past the impressive Paxton House before reaching the coast and the historic harbour town of Eyemouth.

Congratulations – you’ve just Skedaddled the South of Scotland Kirkpatrick C2C. Photos dutifully taken, and bikes loaded up we will then transfer across the border to nearby Berwick-upon-Tweed (approx. 20 minutes) the northernmost town in England.

• Meals: Breakfast

Anyone departing by train on the east coast mainline this morning can do so direct from Berwick-upon-Tweed. The rest of the group will be transferred back to Carlisle (approx. 3 hours including a break), reaching Carlisle by 13:00, where cars can be collected and anyone catching the train from Carlisle can depart. Plenty of time along the way to plan your next Skedaddle holiday!