Chatham does not have a set of organized neighborhoods like major cities but nevertheless there are a variety of differant areas in town that each have their own charm and attractivness.

Downtown: Downtown is centered around Main Street. The heart of Chatham's downtown starts at the Chatham Rotary where Old Harbor Road, Stage Harbor Road and Queen Anne Road run into Main St (Rt. 28). Downtown Chatham is home to an array of shops selling everything from clothes to candy to books to paintings. Main Street is also home to tons of restaurants, there are upscale sit down restaurants, places to pick up a sandwich, coffee shops and ice cream parlors. For travelers who want to stay along Main Street the Chatham Wayside Inn, The Bradford Inn of Chatham,and the Cranberry Inn are all along Main Street (The Bradford is just off Main). The best part of Main Street is that Chatham has not let sprawl invade and as a result downtown Chatham is extremly pedestrian friendly. In the summer time cars have to crawl through downtown and yield to pedestrians. Also every shop or restaurant in downtown Chatham (with the exception of a Dunkin Donuts and CVS) is independantly owned and operated.

Chatham Light /Shore Road: Located on the eastern side of town along the Atlantic Ocean the main road is Shore Road and Main Street (Shore Road actually turns into Main Street when traveling from the Chatham Fish Pier & Chatham Bars Inn towards the Chatham Light). Some of the towns finest homes are located along this stretch of home as well as the Chatham Light & Lighthouse Beach, Chatham Bars Inn, Chatham Fish Pier, Hawthorne Motel and the  Surfside Motor Inn (On Holway Street).

Quitnesset / Mononomy Island: Located at the southeaster tip of town Quitnesset is a private community that is also home to the Monomoy National Wildlife Refuge. Quitnesset is a penninsula with one road (Morris Island Road) leading onto it. Besides the wildlife refuge the island is all residential with lots of trees surrounding secluded and in some cases gated homes. In all the Monomoy National Wildlife Refuge encompasses 7,604 acres with the main entrance being on Quitnesset. The refuge streches over North and South Monomomy islands. At the southern tip of Monomoy is the Monomoy Point Lighthouse which is on the National Register of Historic Places and was restored in 1988. The Monomoy Island Ferry, one of the companies that gives seal cruises departs from the area around the wildlife refuge.

West Chatham: Located to the west of downtown Chatham Route 28/Main Street runs through west Chatham and on and around this stretch of road are numerous restaurants, stores, markets, and offices, many of which are local Chatham Favorites. For example the Chatham Seafood House & Isobar, RooBar, Chatham Village Market, Marley's, Kream N Kone, Marion's Pie Shop of Chatham, The Pampered Palate, Cuffy's of Cape Cod, Christmas Joy of Chatham, Monomoy Salvage, Chatham Liquor Locker and Chatham Antiques. Along George Ryder Road just off Route 28 is the Chatham Municipal Airport. The airport is home to Cape Aerial Tours where visitors can go up in the air over the Cape and visitors can also get flight instruction. On site at the airport is the popular Cloud 9 Cafe which is open for breakfast and lunch.

Chatham Port/North Chatham: Heading north of the Chatham Bars Inn on Shore Road towards Orleans, Truro and Provincetown are the areas of Chatham Port & North Chatham. There are many residential areas in these sections of towns but there are also some beutifuls inns, some great shops & restaurants and some wonderful views of the water and Chatham. Along Route 28 (also Shore Road for a bit) is the popular Campari's Bistro and Benedetto's at Campari's. For lodging in North Chatham there is the Moses Nickerson Inn which is minutes from downtown and Chatham Light. Along Orleans Road/Route 28 is Pleasant Bay Village  which is near the water and the Eastward Ho Country Club. To rent a bike Monomoy Sail & Cycle is located near Campari's & Benedettos on Route 28. Located off of Route 28 on Fox Hill Road is the picteresque Eastward Ho Country Club and the Chatham Yacht Club (on the grounds of the Eastward Ho Country Club).