A Guide to Chatham's Main Street and Beyond

Chatham is one of (if not the most) walkable towns on Cape Cod. It’s also one of the most endearing, combining a classic “Main Street” atmosphere with modern amenities and a wide variety of destinations.

Since the center of Main Street is only a 15-minute walk from Chatham Bars Inn, we wanted to break down all of our favorite walkable must-sees for our guests. When you’re ready to take a break from the beach, make one of these venues your destination!

Cultural Destinations

Despite having a population of just over 6,000, Chatham is full of cultural destinations guaranteed to wow any visitor. From film to theater to fine art, you’re sure to be entertained and inspired.

_Image courtesy of The Orpheum Theater_

**Orpheum**

637 Main St., Chatham, MA 02633

(508) 945-4900

[http://www.chathamorpheum.org/](http://www.chathamorpheum.org/)

The Orpheum Theater opened back in 1916 and, for 72 years, gave locals and tourists alike a place to gather and enjoy the silver screen. When the movie theater shut its doors in 1987, it left a cultural void in Chatham and Cape Cod at large.

Fortunately, in an effort spearheaded by founding president Naomi M. Turner and a team of local volunteers, the Orpheum was completely restored and re-opened in early 2013. The theater retained its classic vintage feel but gained the state-of-the art technology necessary to show first-run movies as well as classics such as Jaws and Raiders of the Lost Ark.

_Image courtesy of The Monomoy Theater_

**Monomoy Theater**

776 Main St., Chatham, MA 02633

(508) 945-1589

[http://www.monomoytheatre.org/](http://www.monomoytheatre.org/)

Fans of the theater should make a point of taking in a show at the charming Monomoy Theater during their time in Chatham. The summer season is jam-packed with first rate entertainment from the classic to contemporary to musicals, with a different show each week from June through August.

_Image courtesy of Gallery Antonia_

**Gallery Antonia**

1291 Main St, Chatham, MA 02633

(508) 469-4020

[http://www.galleryantonia.com/](http://www.galleryantonia.com/)

Chatham’s local art scene is rich and varied, heavily inspired by the gorgeous landscapes of Cape Cod. If you’re looking for a gorgeous piece of art to take home to remember your trip to Chatham, or if you just want to surround yourself with beauty, make sure you check out Gallery Antonia on Main Street.

Food & Drink

Chatham Bars Inn features a variety of world-class dining experiences, including [fine dining at STARS](https://www.chathambarsinn.com/dining-areas/stars/), [upscale pub food at the Sacred Cod](https://www.chathambarsinn.com/dining-areas/the-sacred-cod/), [coastally-inspired seafood at the Beach House](https://www.chathambarsinn.com/dining-areas/the-beach-house/) and a host of [private dining options](https://www.chathambarsinn.com/dining-areas/private-dining-at-the-captains-table/). If you’d like to stroll into town for a meal or a cocktail, however, you’ve got plenty of options.

_Image courtesy of The Impudent Oyster_

**Impudent Oyster**

15 Chatham Bars Ave., Chatham, MA, 02645

(508) 945-3545

[https://www.theimpudentoyster.com/](https://www.theimpudentoyster.com/)

If you’re ready to eat, get to the Impudent Oyster. Their focus is on local seafood, and plenty of it. The generous portions are sure to satisfied the hungriest diner, but don’t be fooled by the large plates: this is upscale dining at its best. Despite prevalent rumors to the contrary, the building was never a church. Formerly a local fisherman's hangout called The Sign of the Surf, it was renovated under new ownership using reclaimed pews and stained glass from a church in Maine.

_Image courtesy of The Chatham Squire_

**Chatham Squire**

487 Main St., Chatham, MA, 02633

(508) 945-0945

[http://www.thesquire.com/](http://www.thesquire.com/)

We’ll be the first to admit that Chatham isn’t known for its rowdy nightlife. If you’re looking for an evening out