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Chatham is located at the elbow of Cape making it fairly easy to reach attractions on both the upper and mid cape regions.
Provincetown - Located at the the very end of Cape Cod Provincetown is about a 45 minute ride from Chatham and well worth the visit. Provincetown is a thriving little town that is also a Gay mecca but that is nevertheless popular with everyone from families to grandparents to international visitors. Why is it so popular? Provincetown is always busy. Downtown Provincetown is centered around Commerical Street which is road that is filled with shops, restaurants, galleries, clubs, B&B's, book stores, souvenier stores and basically anything you could ask for. The streets of Provincetown are all very narrow making walking the transportation of choice and Commerical Street is no exception where pedestrians rule the street. The Provincetown scenary is also amazing with the the shoreline located right behind Commercial Street. For a great view of the edge of the Cape climb up the 252 foot granite Provincetown Monument known as the Effil Tower of Provincetown. Provincetown is place you have to visit just beware that during the summer months traffic on Route 6 can be very heavy heading into Provincetown so leave early and be advised that parking is very limited so be prepared to pay for parking (there is a public parking lot that if you arrive early you can park in...at a cost)
Hyannis - About a 35 minute ride to the west is the town of Hyannis which is home to a wonderful Main Street and waterfront district. Main Street in Hyannis has truly come to life over the last 15 years and is home to tons of shops including the flagship Purtian store, restaurants, cafe's, B&B's, hotels, ice cream shops (including Ben & Jerry's) as well as the John F. Kennedy Hyannis Museum. After visiting downtown and the waterfront area take a ride over to take a tour of the Cape Cod Potato Chip Factory at 100 Breed's Hill Road where youl will get sample's and you can stock up at the gift shop.
Nantucket - One of two islands off the coast of Cape Cod (the other being Martha's Vinyard) Nantucket can be reached by boarding a Freedom Line Cruise at 702 Main Street/Route 28 in Harwich (the next town over from Chatham!). Nantucket was once a thriving whaling port and has now been named a National Historic District filled will seaside cottages and street lamps. While on island bring a bathing suit and take in a swim at one of the fine sandy beaches or if your more adventerous try your hand at windsurfing or get a sailboat. After the beach head to town and visit the towns botiques, art galleries and museums and if its the right time. If you happen to be on the island in June also be to visit the Nantucket Film Festival. Nantucket is truly a gem and a tribute to architectural preservation and is surely worth a visit.