Pickering, Helmsley and Whitby

Hey, Mustlovedogs, first, I'm going to direct you back to this post (which I think you've seen), because there were a LOT of good suggestions for Yorkshire Dales and North Yorkshire lodging in here. https://community.ricksteves.com/travel-forum/england/moving-on-to-yorkshire

Just so I'm clear, though, you will be staying in Grassington in the Yorkshire Dales, then you are looking for a place in North Yorkshire for 3 days (or is it nights)? Then after that you will spend the rest of your time in York. Is that correct?

I loved Whitby and it's a charming place right on the sea with a lot of history and interesting sights to see. But it is not very central (as Carroll pointed out) and would probably be crowded in July. I was there in late September, and don't remember it being that crowded but that was also 25 years ago when there was not nearly as much congestion as today.

Pickering could be fun because it has the North Yorkshire Moors Railway, which looks very interesting and I'm hoping to ride it. In fact, if you stayed in Pickering, you could take the train to Whitby and spend the day there. Not sure about logistics but I'm sure you will get some other responses that might add more info to that. :-)

mardee, yes, that thread you started is full of great information; I am using quite a bit to help learn about where to visit. I don’t want folks to feel I am asking them to take the time to revisit/reply again the things they shared with you for your upcoming trip and I truly hope I am not being wearisome. A factor that I think may come into play in advising us where to stay for our trip is we aren’t driving. Maybe it’s not that big of an issue.

Just to clarify, my current plan is to fly into LBA from IAD. Train/ bus to Grassington. Spend 4 days there, move over to a base in the Moors for 3 days, then go back to York for three, one of which I was thinking a day trip by bus to Thirsk. We’d then taxi or public transport back to LBA to fly home.

Does this seem doable? Still too much moving around? York didn’t get enough of our time from just a day trip this past summer. We’d really like to spend a night or two just to be there in the evening without the crowds and see some of the things we missed.

I’m open to any and all suggestions and advice!

All three are well worth visiting and are very different. Whitby is probably the busiest, especially during the summer. It is popular for day trips as well as longer stays. Streets are narrow with narrow pavements (sidewalks) particularly in the old town and climbing up to the Abbey. There’s lots to do and see there with the ruined abbey, St Mary’s Church and the harbour area. There are also the Dracula connections too. There is a real buzz to the place.

Helmsley with its ruined castle and walled garden possibly has more of a tourist feel to it than Pickering. With the river flowing through it, it does rather remind me of a Cotswold town... Pickering has more shops and still retains the feel of a busy traditional market town used by locals. It also has a ruined castle and the church is well worth visiting for the wonderful medieval wall paintings. Beck Hole Museum is also worth a visit. It is also the terminus of the North York Moors Steam Railway - not only is it a super run, it will also take you to Whitby!
Russell's bakery and cafe on the main street is highly recommended - get your picnic supplies from here.

Two other small villages you may like are Thornton le Dale with its stream running through the centre and Hutton le Hole, again with a stream and the Ryedale Folk Museum. However these probably are more restricted as a base. My choice would be for Pickering followed by Helmsley - but that is very much a personal choice.

Slow Europe Forum have a lot of travel articles about Yorkshire and there are ones about the places you mention with lots of detail and pictures.

I agree with Wasleys, but for practicality without a car.
Helmsley is a long hourly bus ride back from Scarborough or 2 buses a day from York.
H le Hole has no real bus service.
T le Dale and Pickering are both on the Coastliner bus route from Leeds and York to Whitby. Hourly as far as Pickering and TLD, every two hours onto Whitby.

I'd be happy in either, but Pickering is the bigger with all facilities, so likely gets my vote

Thank you so much for this additional information! The link to the slow Europe forum will be a hit and I am sure over Thanksgiving at least one, if not both, of my travel partners will be saddled up beside me on the couch looking at this IPad and the places you’ve suggested! Even the names, Thornton le Dale and Hutton le Hole, sound fun!

I really think the NYM Steam Railway would be a highlight of the trip. I can’t wait to hear about mardee’s experience when she goes. Crazy as it may seem, I’m looking at weather patterns of the area on weather underground to get info on either June 11-21 or July 1- 12. (2025- don’t judge 😉) Not sure if there is a better time between these two timeframes, but they each could work with the kids’ holiday vacation days.

Thanks again for taking the time to share your thoughts on everything. You all are the best!

We spend a night in Pickering then drove through the Yorkshire Moors to Whitby and loved that experience.

I highly recommend those articles in Slow Europe on Yorkshire that wasleys linked. There is a lot of information in there and they are very well written.