Travel Guide: Chatham and Provincetown, Cape Cod, MA

We recently travelled to Chatham, Cape Cod for a week long vacation with the family. Chatham is a picturesque New England town with the most charming downtown area full of shops and restaurants. My hubby and I also got to sneak away to Provincetown for a day and a half to celebrate my birthday. ☺️
Here’s what I recommend checking out if you are traveling here:


Things to do:

  1. Chatham Pier: Go to the Pier and get a lobster roll.  This was probably the best lobster roll I had during our trip and I think we averaged one a day. 😉  Also, the restaurant at the pier will prepare whole lobsters for you if you put in an order.  We did that one night for dinner and they were delicious. It was my first time eating a whole, cooked lobster and it was quite the experience! See evidence below:

2. Main Street: The downtown area is a wonderful place to walk, do some shopping, dine and get some ice cream.  [We had the best ice cream at Emack and Bolio’s! I highly recommend a visit here.]  Here are some things to check out:
    • Ducks in the Window – this is a fun little shop filled to the brim with small to large yellow ducks.  Cute for a kid stop and photo! 
    • Art Galleries – there are so many beautiful art galleries that you can pop into as you stroll down Main street.  If you’re looking for artwork that’s got more of a coastal influence, this is an amazing place to do some [high-end] shopping.


Traveling with a toddler means you need access to a kitchen and a grocery store [ideally, of course!]  So we stayed in a rental house and cooked a lot of our meals. However, we did make it out to a few places that we really enjoyed!

  1. Pisces: If you’re looking for fine-dining in Chatham, I cannot recommend this place enough.  We came here the night of my birthday.  It’s a quaint little restaurant that looks like it was somebody’s home many moons ago.  The space is limited but the ambiance is cozy and warm.  The food was also fantastic!  As a sidenote, I still can’t believe we took a toddler here and survived.  Ha! There were many walks outside that my husband, myself and in-laws took to get some of his energy out.  It’s definitely not a restaurant that caters to kids [they do not provide high chairs], but they were such good sports and really took care of us.  

  2. Chatham Squire: This restaurant is a landmark in Chatham.  The food and service were great and they were so sweet to us even though half of my one year old’s dinner ended up on the floor. It’s right on Main street and is very casual and family-friendly.

  3. The Talkative Pig: The pizza at this restaurant was so delicious, my in-laws came here twice! [We went once and loved it.] 

  4. Village Market: While not technically a restaurant, I wanted to include this place! This small grocery story is convenient and easy to navigate.  It reminded me of a cross between a small Tom Thumb and Central Market [for all of you Texas girls.] It’s got specialty items, regular food and a counter where you can pick up ready-made pastas, salads, etc.  It’s great if you need a quick meal on the go or if you don’t want to make your way through a large grocery store.  

  5. While we did not go to these two restaurants, they are on my list to try if we make it back to this magical little town: Wild Goose Tavern & Impudent Oyster.  One night when my husband and I went out for an impromptu dinner on our own, we tried to get a seat at Wild Goose Tavern and there was a 45 minute wait.  We read great things about this place online and it was packed! They have a fun patio out front that’s great for people watching on Main.  We then made our way to Impudent Oyster and they also had a long wait! So we went to the bar and hung out for a bit until we decided to just hop over to the Village Market for some bread and spreads to avoid the wait.  However, the bar and restaurant were both packed at Impudent Oyster and the food we saw looked great! [Moral of the story: always make a reservation in Chatham – especially on a Thursday – Sunday when the town gets packed with visitors.]  


  1. Baseball Game: The Chatham Anglers is a collegiate summer baseball team that’s based in Chatham and we got to enjoy a game one night! We had a wonderful time.  You can buy concessions, t-shirts and enjoy a ballgame in the beautiful weather. 
  2. Butterfly Exhibit: We absolutely loved this place! We went to the Butterfly zoo and got to feed the butterflies.  They were flying all around and even landed on us at times.  The monarchs and other species were a sight to see.  This exhibit also housed caterpillars and the guide talked about the lifecycle of the butterfly. A neat activity for kiddos and adults!  One thing to note is that the exhibit is about a 30 – 45 minute drive from Chatham.  


For my birthday, my husband and I snuck away for a night and went to P-town, which is a completely different experience from Chatham.  Provincetown is lively and is known to get a little wild! There are tons of bars, shows and clubs which provide for an avid nightlife.  I think we were in bed by 11 pm, but still got to enjoy it thoroughly! 😉 
Provincetown has a population of about 3,000 and feels so tiny and intimate.  The main downtown area [i.e. Commercial Street] is where you stay, eat and stroll during your visit.
Things to do

We were only in Provincetown for one night and we mainly stayed in downtown.  There are plenty of art galleries and stores where you can window shop.  You can also walk along the water as it lines Commercial Street.  It was recommended that we do a sand dune tour or go dolphin/whale watching, but we just didn’t have time during our short trip!


The bed and breakfast that we stayed at was so wonderful and I highly recommend it! We ate breakfast here, which was lovely.  The owners had a spread of croissants, fresh cheeses, fruits, cereals and more.  There was also a coffee station with all of the fixings.  Here’s a view of the eating area:

The restaurants we went to were:

  1. Pepe’s: We came here for a before-dinner drink and snack and it was both delicious and beautiful! We sat at the bar and got to watch the sunset over the water.  The restaurant overlooks the Provincetown harbor and we had great service.  I almost wish we had stayed to eat dinner here because I enjoyed the ambiance and view so much. 
  2. Strangers and Saints: this is a tapas-style restaurant where the meal comes out in shareable plates.  We sat on the front patio, which was nice as we had a direct view of all of the happenings on Commercial.  I will also mention that my husband thoroughly enjoyed his cocktails here, if you’re wanting to get a drink with dinner!
  3. Purple Feather Cafe & Eatery: we had the BEST gelato here! It’s all made on site from scratch and they have amazing desserts as well.  My husband’s cousin owns this restaurant so they treated us to lunch – I recommend the mushroom soup if you’re in the mood for something warm, hearty and spectacular. 🙂 Even if you aren’t hungry, I suggest peeking in and seeing the naughty decor and treats. 😉 
All in all, Chatham was a magical little town that I hope to return to in the future.  It’s quaint and lovely and makes you feel at home.  Provincetown was so different and wonderful in its own, quirky way.  I hope these recommendations help you if you’re planning a trip to the Cape.  And if you have any places that you love, I’d love to hear about them in the comments below.

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