Time of year for Scotland trip

If you are planning to be in the countryside I would go for August and September, once the midge frenzy is over. It relly can be unpleasant in June

If it was me i would go to Scotland in September since it averages similar weather as June, and it could be a little less crowded. I'd skip August for the same reason. The daylight hours are longer in June if you plan to hike, etc, August is the peak bloom for Heather. If you are driving you can visit less crowded places. We usually stay in B&Bs in the countyside and small hotels in the cities. Check out www.visitscotland.com for a good gateway site. Be sure to make reservations for Skye as soon as they will let you,

That's pretty much the end of the Highland Games Season, but you still have-
2 September Braemar Gathering;
3 September Blairgowrie and Rattray Highland Games- that one may particularly suit you given your heritage
and
9 September Pitlochry Highland Games
(These are all 2023 dates, but Blairgowrie is always the first Sunday after the first Saturday in September- so the earliest possible date is 2 September, the latest is 8 September, which it is in 2024), Braemar is 7 September 2024, Pitlochry is 14 September 2024

I went in September to avoid the tattoo and fringe festival crowds, and to attend the Braemar games, which I quite enjoyed. It was a little cool at times, and had a couple of quite wet days, but otherwise fine, and I never really encountered bad traffic.

We have enjoyed several road trips around Scotland, all of them in June. June daylight hours are much longer than those in September. We have never been bothered by midges. I don't know what the little critters' schedule is in Scotland, but a guide in the Canadian Rockies told us they don't hatch there until late June. If you check out sites such as "Walk Highlands" you can find lots of information about avoiding the little critters.

Regarding midges. They are mainly to be found in the west and Highlands/Islands. I can report that they are here now and will be here until mid September at least. They are mainly a problem in shaded and damp areas and at dusk. Bright sunlight and/or winds above 5 mph gets rid of them.

If I had your choice of dates I'd go for June as the weather in August (here on Skye at least) tends to be very rainy.

As a rule, we don’t travel June-August due to it being major tourist travel time. Of the months you stated, September would be my choice.