Downtown, with one easy detour
This is a compact crawl you can walk in an evening. It is less a Crown Street bar route than a downtown loop with a single detour, which keeps the distances short and the night from turning into a project.
Start with coffee at Atticus Bookstore Cafe, 1082 Chapel St. It's a downtown bookstore-cafe and one of those addresses that works whether you're meeting someone or just killing half an hour.
From there, head west on Chapel to Olea, 39 High St. The listing is straightforward: Spanish and Mediterranean food, with a focus on tapas. If you're building a crawl, small plates make sense.
If you want to keep the walk tight, stay downtown and go next to Bar, 254 Crown St. It's part bar, part pizza stop, and it's a practical late stop if your group wants to shift from dinner into drinks without changing neighborhoods.
For a final stop, you have two reasonable directions. If you want cocktails, Ordinary New Haven, 990 Chapel St, keeps you downtown. If you want to make the crawl more New Haven-specific, walk up to Modern Apizza, 874 State St, in East Rock.
That's it. Four stops, and a route you can adjust depending on whether your night runs more toward coffee, tapas, pizza, or cocktails.