Last we went to Henry’s was maybe 6 months ago and food was fine as before. I believe they are a Michelin recommended restaurant for what that’s worth. Their wine list is interesting as they are also a wine club. They have half-priced wine on Wednesday.
As for others, besides establishments already mentioned, there’s also The Berczy Tavern at Yonge/Church which is not as close to you as Henry’s but they have an interesting selection of wine as well. They are also a piano bar so you also get the benefit of live music if this suits you. They have Sunday Roasts (Prime Rib) with selected half-priced wines and cocktails. They also allow BYOW with reasonable corkage.
I wanted to update you all because I had so many suggestions and I looked into all of them. We are now back from our short 4 day trip to Toronto. Based on weather, location and other things, we ended up going to And/Ore, which was suggested on here by @Estufarian . It was really great. We went upstairs and had the chef’s picnic which was exceptional. Really interesting and fun; well balanced flavours and lots of different things to snack on. We had just finished it when the second (hot) course came and we had forgotten it was coming so couldn’t do it justice. Truly delicious salmon and a potato pavé. The room was so lovely with a great atmosphere and it was just so nice to be somewhere so different to a usual dining room. Staff were helpful and relaxed and efficient and as we were there early the chef came to chat along with one of the co-owners. As for wine - I had the champagne flight which was very good. We discussed Canadian wines and they brought us one they were thinking of trying which was a Pearl Morissette orange wine, on the house. All in all a memorable night for us.
As an aside, we visited Tawse and had a great tasting, and Domaine le Clos Jordanne’s pinots were fantastic. The room was lovely - would recommend. Thanks to all for your tips which made our trip special.