Dog Friendly Adventures in Helmsley: A Perfect ‘Walk-Inn’ break

It’s no secret that we absolutely adore our stays with The Inn Collection Group! With their inns perfectly nestled in stunning locations across England and Wales, finding the ideal getaway and fantastic deal is a breeze. Honestly, it feels like we’re on a delightful adventure, gradually exploring every single one of their beautiful inns, and this marks our sixth stay with them—each visit has been nothing short of perfect! For our Easter escape, we chose The Black Swan, situated in the heart of the picturesque market town of Helmsley, North Yorkshire. We opted to experience one of their ‘Walk-Inn’ breaks, and I couldn’t be more thrilled with our choice. If you’re seeking unbeatable value for a dog-friendly retreat, this deal is for you!

What was included:

  • A two night’s stay (based on 2 people sharing)
  • A meal allowance of £26 per person for the first night
  • Two hearty breakfasts each morning to fuel your days of exploring
  • Dogs stay free
  • A complimentary walking guide of local walks in the area.

We chose a cosy double room when booking, and it was perfect – complete with a generously sized ensuite featuring a shower and delightful complimentary tea, coffee, and biscuits (standard when staying with them). At the end of our first day, we enjoyed our evening meal, for which we had reserved a table upon check-in. The £26 allowance let us indulge in both a main and a dessert each. Due to our meal choices, we did need to contribute £2, which was added to our room bill, but I am sure if needed you would have been able to enjoy both within the £26 budget. Another new feature we were offered, aimed at guests staying more than one night, is the option to forgo room cleaning in exchange for a complimentary drink. This thoughtful initiative not only enhances the guest experience but also promotes sustainability within the company. A nice idea.

For breakfast each morning we had the choice of croissants, toast, juice, tea & coffee and an option from the cooked breakfast menu. I sampled the eggs Benedict the first morning, followed by a full English the second. All made with local produce and the perfect way to fuel up before a day of adventure. As we are early risers we chose the best spot for breakfast with a huge window overlooking the market square. As with all Inns, your dogs are welcome to accompany you when eating and dogs were welcome in the non-carpeted areas of the Black Swan.

Top Tips

Check-in is at 3 PM. We arrived early and inquired at reception regarding the possibility of early parking, which they happily accommodated. The three spaces directly in front of the Inn are designated for The Black Swan; therefore, it is essential to display your slip from reception clearly, as ticket inspectors frequently monitor the vehicles. The Inn offers plenty of additional parking spaces located at the rear, accessible via the side street.

The Black Swan has a ‘Hidden’ beer garden which we didn’t actually check out so if anyone reads this and has been, please let us know what it is like. Due to having such a great time exploring we didn’t get a chance to enjoy a drink there.

Exploring Helmsley

We had visited Helmsley briefly a couple of times after walks in the area, but staying the weekend truly allowed us to uncover all that the town has to offer. We were fortunate to choose the ideal weekend, with the sun shining throughout, which is a bonus on our dog-friendly holidays.

On the first day, after we had parked up, we wanted to take the spaniels on a lovely walk and had decided on walking to Rievaulx Abbey. If you didn’t know, Helmsley marks the start of The Cleveland Way, a 109 mile trail that takes you over the North Yorkshire Moors, along the North Yorkshire Coast until you reach Filey Brigg. We actually met someone at the start of the trail who was about to walk the whole trail at once – I took her photo to mark the start of her journey. For others, like us, it can be chosen to be completed in sections and this is the second time we’ve walked along part of the trail. See our blog post Coastal path Hike – this is also part of The Cleveland Way. This scenic walk between two historic sites, Helmsley Castle and Rievaulx Abbey takes you on a trail once walked by the monks of the Abbey. You may also choose to visit Helmsley Castle with your dog on a short lead and discover the interesting facts of the medieval ruins.

Helmsley Castle

You will find the start of the trail next to the Long Stay Carpark – if you are visiting just for the day this would be where I would recommend parking.

The trail itself is an easy 2.5-mile journey to Rievaulx Abbey. It’s the kind of walk I particularly enjoy, as it provides ample opportunities to let the spaniels off their leads to roam freely. The trail meanders along picturesque rural paths, winding through lush woodlands and running alongside the River Rye. Along the way, the views are truly lovely, showcasing the beauty of the Rye Valley. Finn and Bobby, especially enjoyed splashing around in the cool waters of the river when we finally reached it on that warm spring day. As we approached Rievaulx Abbey, its stunning architecture came into view, set against the backdrop of an extraordinarily tranquil landscape. It’s no wonder the monks chose this serene location to find solitude and peace, as the atmosphere is wonderfully quiet and calming. The Abbey is an English Heritage site and dogs are warmly welcomed to enter with you, provided they remain on a short lead, making it an ideal outing for dog owners. For more information on visiting, including ticket prices, click here. After taking some time to explore the Abbey, we took the same route back to Helmsley.

Dog-friendly places to eat & drink

We were absolutely thrilled to discover that most places welcomed dogs, and with the weather being nothing short of spectacular—a rarity during school holidays—we couldn’t resist seizing the moment! We embarked on our very own exciting dog-friendly pub crawl. Here are our favourite spots:

We visited most of the pubs during our visit. At Helmsley Brewery, we discovered a treasure—a fabulous spot with a charming beer garden that was such a little suntrap. It was perfect for those who truly appreciate the art of brewing, as they craft their own exquisite beers. Next we took the opportunity to grab a seat outside The Feathers Hotel at The Pickwick Bar, an ideal spot for people-watching across the bustling market square.

On our second night, we chose to eat at The Royal Oak for some classic pub grub. Dogs are welcomed both inside and out! The staff were really friendly and even spoiled Bobby and Finn with some treats, which they loved! The food was tasty—we each got a main and dessert, and it didn’t cost a fortune, which is always a nice little win.

If you’re looking for a spot with a view, check out Number Twelve — it’s a chill cafe-bar-eatery on Castlegate. We grabbed a drink there. The food looked amazing! Plus, your dogs are welcome both inside and outside. The vibe was really relaxed, and the view was just perfect.

You can’t visit Helmsley without checking out a few independent shops! Our top picks? First up is Barney and Stan’s Pet Corner, where the spaniels totally loved some doggy ice-cream in the sun. Then there’s Thomas the Bakers, which has the yummiest fresh pasties and cheese scones (I even took some home!). And don’t forget Helmsley’s own Traditional Sweet Shop for those classic old-fashioned sweets that remind you of your childhood.

If you’re planning a visit to North Yorkshire with your dog, Helmsley is undeniably a top choice. This charming town boasts a relaxed atmosphere, and the locals are incredibly friendly. Whether you decide to stay in Helmsley itself and enjoy the scenic walks directly from town, or use it as a fantastic base to explore the wider region, you won’t be disappointed.

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