Chatham / Cape Cod Guide

This post has all of my recommendations for Chatham, Massachusetts! If you’re looking for a family – friendly New England beach town with great shopping and seafood, this is the place to go! 🦞

Map

First, let’s get our bearings. 🤣 Here’s where Chatham is on a map. It’s about a 2 hour drive from Boston, and it’s about half way down the Cape.

Getting There

If you’re flying, the closest major airport to fly into is Boston (BOS), but there are also a bunch of other closer, smaller airports. You can check flights below. From the Boston airport, it’s about a 2 hour drive to Chatham.

Getting Around

I’d recommend renting a car because you’re going to need to drive to a lot of the things that I mention in this post. You can check out car rentals here.

Where To Stay

1. Rent a House

One option is to rent a house with Pretty Picky Properties, and the house we rented was near the downtown.

• View available rentals on Pretty Picky Properties here

2. Chatham Bars Inn

If you want to stay in a hotel, and have the resort experience, I would recommend staying at the Chatham Bars Inn. It’s right on the water, has a private beach, a pool, and restaurants.

• Make reservations here

3. Wequassett Resort

Another great option is the Wequassett Resort. It’s technically in Harwich, which is a town about 10 minutes away, but it’s also a nice option with a pool, restaurants, and a beach area.

• Make reservations here

Best Things To Do

1. Fish Pier

You should definitely check out the Fish Pier, you can order steamers and lobster, and there’s also a market attached to buy fresh fish and seafood. You can also sometimes see seals, since they swim up to the boats right by the pier!

• Website here

2. Shopping in the Downtown

Downtown Chatham is pretty huge for a beach town, you could spend an entire day just shopping around the downtown!

3. Morris Island Loop Trail

This was a fun walking trail to go on, it’s right along the water so it’s not really a dirt path, it’s more of a sand path. It’s kinda hard to find so be aware of that, but I’ll post a picture of the path entrance below.

4. Beach

There are a bunch of different options, but the beach we liked the best was Ridgevale Beach. It had lifeguards, bathrooms, a food stand, and a shallow area for young kids. The water wasn’t super cold either, so that was nice too. If you have infants or toddlers, I’d recommend checking out Skaket Beach, which is a little further away, but it’s really shallow so good for families with young kids. I’ll put some pictures of both beaches below.

5. The Beachcomber

This is a bar / restaurant next to a beach and has great vibes. This is where you wanna get a piña colada. 🤣 A few important things to know are 1. The parking is terrible, it fills up around 10am, and if you don’t get a spot, you’ll have to park like a mile away and walk so that’s not ideal if you have kids and a bunch of stuff to carry. and 2. It’s on a giant hill, so again, if you have kids and a bunch of stuff to carry, you’ll have to carry everything up and down it, which can be pretty exhausting. Overall, I really enjoyed it and would definitely recommend going, but just be aware of those things, especially if you are making a long trip to get there.

• Website here

6. Rent Bikes

Another fun thing to do in Chatham is to rent bikes. We used the Wheelhouse Bike Co. and went on a trail close by. I wouldn’t really recommend the trail because it was a little choppy, like there were streets that you had to cross pretty often, so it was kinda difficult to manage with 2 young kids. If we ever go back to Chatham, I think what we would do is get bikes delivered to the house we were renting, and just bike around the neighborhood.

Best Restaurants

1. Chatham Bars Inn

• Make reservations here

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A post shared by Top Oceanfront Resort Cape Cod (@chathambarsinn)

2. Impudent Oyster

• Make reservations here

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The Squire

If you are into the bar scene, The Squire is the place to go!

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Full Guide

For more tips, check out my full guide here ⬇️

Weather

We went in mid-July, and for the warmest weather and water, I would recommend going mid-July to August.

Average Temperatures (Chatham)

Month	High / Low (°F)	Water Temp (°F)
January	36 / 23	41
February	37 / 24	39
March	42 / 31	40
April	50 / 38	45
May	58 / 47	51
June	66 / 55	60
July	73 / 62	67
August	73 / 64	71
September	66 / 54	67
October	58 / 45	57
November	50 / 37	52
December	41 / 28	46

And those are all of my tips for Chatham! Do you have any recommendations? Let me know in the comments!