<p>Aaaaaaaahhh the Cape!</p>
<p>My college roomies and I summered on the Cape back in the day and we all still return nearly every summer. </p>
<p>Luckily, in May, you won’t have to deal with the summer crowds and traffic jams and it’s not overrun by those annoying college students!</p>
<p>So, you’re staying in Chatham? At the lovely Chatham Bars Inn, perhaps? A favorite of mine. It’s off season so definitely a much better deal. They offer all kinds of packages for golf (I think there are like 40 golf courses on the Cape), whale watching, fishing and sailing, etc. Check out the Chatham Squire for dining and entertainment --they have great food and music in the tavern (and I think open mike night is on Thursday?)</p>
<p>In Brewster, check out The Woodshed (owned by friends of mine from college–it’s attached to the Brewster Inn and Chowder House, which is fab.) The Woodshed is a great little “dive” with live music which tends to be “folky.” Also, pretty good comfort food. They also sponsor a 5k race (in August) which is a lot of fun.</p>
<p>For great homemade ice cream–my picks are The Smuggler (near the Village Green) in Dennis (try the French Raspberry Truffle) and The Sundae School (quaint and old-fashioned–opened when I was in college) in Harwich Port or East Orleans (try the Blueberry) and the Highland Creamery (fun and funky decor) in Truro (on the Nat’l Seashore–try the Chocolate Heart Attack!) </p>
<p>And don’t forget to watch the sunset at Nauset Beach–very romantic! </p>
<p>Enjoy.</p>