The Wayside Inn in the perfect combination of classic white clapboard New England inn--it is on an original Stagecoach route--and upgraded, boutique-style inn with fireplaces and jacuzzis or private patios featured in many rooms. Their pool is nice sized with a patio for those days when the Atlantic's a little too "bracing". Located at the center of the charming main street and next door to a park that features Friday night band concerts in summer, it's close to plenty of shopping and walking distance to the beach and the light house. The food at the inn is first-rate in a pleasant, bright dining room with unique murals and a winter fireplace. This is our family's go-to for special occasion and holiday meals and we refer out-of-town visitors for super accomodations. The owner of the inn lives in town and takes an active interest in the operation--a pleasant alternative to chains. It costs more but it is worth it--beautiful, handicap accessible, and well staffed. One Warning: lots of weddings here; be sure to ask when booking & if you don't want reception noise do not book the main inn--ask for the annex instead--much quieter!
If you golf, the 9-hole municipal course which abuts the famous Chatham Bars Inn is not to be missed.
The Chatham fishing fleet is one of the few left on the Cape--watch the catch come in afternoons.
Don't miss visiting Morris Island, a half hour walk but TOTALLY worth the hike for great walking beaches and fantastic birding. For a unforgettable on-the-water water adventure, take the Seal Watch from Outermost Harbor Tours (right in Chatham) or drive to Provincetown (90 minutes in summer) for a whale watch and amazing National Seashore Beaches.
The Chatham Methodist Church has an excellent concert series, and the Harwich Junior Theatre (next town over) is great for kids of all ages.
For local color check the Chatham Squire across the street-great eats and a funky bar.
The Christmas Stroll is a wonderful way to kickstart your Christmas spirit--usually in the first weekend of December. Great packages--get a fireplace room and relaaaax.
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