Eastern Ave is a good climb. If you get the chance head down Park Ave and go over to Winchester country club and ride around it on Hutchinson and Johnson Roads and then try Waltham St. Trapelo Road from Belmont and out through Lincoln is also a good hill route and you can stop and see the Gropius House.
Yup, you definitely don't need to ride to Worcester County to find hills (although they do keep a lot of nice ones there). Hill climbing is a good way to get warm in cool weather.
rod