Some ideas
I have been to Milford Landing twice. Downtown Milford is hopping at night. There are several bar/restaurants within a very short walk of the docks. The Stonebridge is a very nice restaurant overlooking the river. Live music and a bar outdoors, a bar and white tablecloths indoors. Fairly high-end dining; pricey, but they offer a discount to those docked at the Landing. The outdoor scene at Stonebridge on the weekend is wild. It is clearly the place to see and be seen. SBC Brewery is more casual. I have never eaten there, although I have heard good things about the food. They have a DJ and dancing. It is across the street from Stonebridge, and also overlooks the river. There are several other restaurants, and at least one nightclub in the immediate vicinity. The Landing hands out Welcome to Milford packets with cuopons, discounts, maps, etc. Also, just across the stone bridge from the marina is a public park. I didn't walk over there, but you can see the tennis courts. I do not know if they are available. Milford also sponsors various activities on the Town Green, a short walk from the marina. I don't know if anything is scheduled for this weekend, but I have been to a crafts fair there.
