Cape Cod Itinerary

Cape Cod Itinerary

We just returned from our first vacation as a family of four and honestly, I’m exhausted – LOL! Trips with kids really aren’t all that relaxing but they’re rewarding in their own way and it was nice to get out of the city, leave the craziness of selling the condo/buying the house behind and just spend time together before I head back to work.

Per usual, we dragged our feet on booking anything and then airfare/hotel/rental car prices skyrocketed as summer hit and everyone was finally ready to travel again. Ultimately though, I was pretty set on making it happen since I used up all my PTO [and then some] on leave and don’t know when I’ll get the chance to take time off again.

When it came time to pick our destination, we were pretty torn. I knew I wanted the beach and actually really enjoyed our time on Emerald Isle last summer but wanted to try something different. We looked at rentals in Hilton Head and OBX but I was a bit worried about early hurricane season in the Carolinas – and the humidity there in August – so we decided to look further north and eventually agreed on Cape Cod. It originally aligned with a potential family commitment in NH that fell through but we kept our house rental and ended up sharing it with my parents.

August 13, 2021 – Travel Day [Chicago – Cleveland]

We intended to leave Chicago around noon on Friday but actually didn’t get on the road until just after 3PM. Trying to pack for everyone and juggle a few work commitments that morning put us way behind schedule and we got caught in a lot of traffic leaving the city. We drove for about seven hours – including a few stops to feed Isla and stretch our legs – and made it just past Cleveland. We struggled to find a hotel with availability last minute and ended up at the Quality Inn in Streetsboro which had decent reviews but is not somewhere I would recommend or want to stay again.

August 14, 2021 – Travel Day [Cleveland – Chatham]

Isla woke everyone up around 6:30AM the next morning so we decided to hit the road early since we had a long drive to Cape Cod. We passed through OH, PA, NY and CT before dropping down into the Cape around 8:30PM that evening. It was a long drive but the weather was good, there were plenty of places to stop for food/gas/coffee and the girls did great [I did a whole post on Toddler Road Trip Tips in case you’re interested]. When we arrived, we ordered pizza delivery from Knots Landing Bar & Grill which took about one hour. In hindsight, I wish I had done a little more research on the pizza because there seems to be quite a few better options in the area but there was so much going on when we arrived that I just called the first place that came up on my Google search.

Chatham, Massachusetts
August 15, 2021 – Red River Beach

Our first morning on the Cape was beautiful so after grabbing coffee and donuts from Chatham Village Cafe & Bakery [you must try the cinnamon twist pastry], we loaded up the car and drove to Red River Beach in Harwich [$20 CASH per car], per a recommendation from our Airbnb host. Red River Beach is on the Nantucket Sound so it’s a little warmer than the ocean side beaches. When we visited there was a good amount of seaweed and shells/rocks on the beach but there was also a pretty large area of sandy beach to spread out. Overall, the beach is easy to access from the parking lot, has bathrooms, a small food truck and calm waters but I’d say it wasn’t our favorite of the trip.

[Note: most beaches in Cape Cod do require passes whether you’re walking or driving and I’ve heard that parking lots fill up early. In our experience, you can purchase the beach passes at the entrance but they are CASH ONLY. I believe you can also purchase week long or season long beach passes but we didn’t do that.]

We left the beach just after noon in search of a quick lunch and ended up stopping at Mom & Pops Burgers for takeout. Not sure what possessed me but I ordered a fried chicken sandwich which was fairly unmemorable and Kevin got the burger which he enjoyed. If you’re familiar with Five Guys, it’s a similar burger style. The rest of the afternoon was pretty low key while the girls napped and we waited for my parents to arrive. After my parents unloaded the car and settled in, my mom and I left to grab groceries for the week and something to grill for dinner that evening from Stop & Shop.

August 16, 2021 – Forest Beach

The following day we decided to hang at Forest Beach, the little local beach walking distance to our house. It’s a fairly small beach with a narrow strip of sand that runs along South Chatham on the Nantucket Sound. Similar to Red River Beach, as you get close to the waters edge, there are a lot of rocks and shells so I’d definitely recommend water shoes if you plan on wading into the water. Other than that, it’s a good, no-frills, free beach. There are no bathrooms, lifeguards or food stands but there is a small parking lot and the ice cream truck did come around a few times.

That evening, Kevin and I went on a quick happy hour date to The Impudent Oyster in downtown Chatham. The ambiance is cool because it’s in an old church but there is only indoor seating available. We shared oysters and scallops which were delicious and locally caught. Afterwards, we drove over to Sundae School in Harwich Port and picked up a few pints of ice cream to take home for everyone. Supposedly, they just won best ice cream in Massachusetts and judging by the line, I’d say everyone agrees. We enjoyed the flavors we tried; my favorite was Cookie Monster – vanilla with cookie dough and Oreo.

The Impudent Oyster
August 17, 2021 – Forest Beach

Once again, we decided to stay local and hung at Forest Beach for the day. We got ice cream from the truck when it stopped by and spent the day playing in the sand, flying kites and tossing stones into the water. For dinner that night, we cooked up one of our favorite pasta dishes – Conchiglie alla Sarda – and relaxed at the house.

August 18, 2021 – Heritage Museum & Gardens

By Wednesday, we were ready for a small break from the sun and beach so we loaded up the kids and went to Heritage Museum & Gardens in Sandwich [admission $20 per adult; three & under free]. It was a bit of a drive [~45 min drive from Chatham] but it came highly recommended and turned out to be a great spot with kids. It’s essentially just a really pretty outdoor garden walk with a few different displays. They have a Vintage Automobile Collection and New England Toy exhibit that we skipped in favor of exploring the gardens, fountains and Hidden Hollow kids play area which was incredible! It’s all outdoors and includes various stations where kids can “climb stepping stumps, navigate log balance beams, construct forts, create nature-inspired art, build with blocks, dig in sand, experiment with water, make music, engage in sensory investigation with plants, and more.” Palmer loved it and it felt like a COVID safe activity!

We got back to Chatham around lunchtime so we had a quick lunch at the house and then spent the afternoon hanging at Forest Beach again. For dinner that evening we ordered take out from The talkative Pig which was just across the street from our neighborhood. It’s tough to judge a restaurant on their takeout because things tend to lose their magic once boxed up but I think everyone generally enjoyed their meal. If I were to eat there again, I would definitely want to try the pizza. We didn’t because the wait time was double to add one but I’ve read great things about it.

August 19, 2021 – Head of the Meadow Beach

On Thursday the overcast skies and rain that was forecasted but kept getting pushed back finally caught up to us. Even knowing this was likely, we made plans to visit Head of the Meadow Beach in Truro [~45 min drive from Chatham; $25 per car]. Due to the weather, we pretty much had the beach to ourselves and had the best morning walking along the shore, wading in the water and exploring the dunes. Of all the beaches we visited, Head of the Meadow was my favorite. It has bathrooms, lifeguards and a wide, long stretch of sandy beach with very little seaweed and rocks making it much more comfortable to walk on. It is, however, on the ocean side so much cooler than the Nantucket Sound, and we did see seals so you know the sharks can’t be that far off shore.

Right before the rain really started to come down, we packed up our beach gear and made our way back to Chatham to watch the seals come in with the fishing boats at the Chatham Pier. We grabbed food to go at the Chatham Pier Fish Market – lobster rolls, clam chowder, lobster bisque, clam strips and scallops – and rendezvoused at the house for a late lunch/early dinner.

August 20, 2021 – Art Festival & Nauset Beach

On our last full day in Cape Cod we headed into town for the 50th Annual Festival of the Arts, a free festival showing “the work of 120 fine artisans and craftsmen presenting their original and handcrafted artwork, jewelry, fabric, pottery, fashion, wood, glass, metalwork and so much more.” It reminded me a lot of the Old Town Art Fair if you’re local to Chicago. After that we strolled around to some of the shops downtown and grabbed lunch at Public Cafe to eat back at the house.

That afternoon we took the girls to Nauset Beach in Orleans [~20 min drive from Chatham; $30/car], another ocean side beach. Since it was a sunny day, the beach was pretty crowded but we arrived later in the afternoon and had no trouble getting parking or finding a spot on the beach. In terms of style, it is very similar to Head of the Meadow – wide sandy beach with bathrooms, lifeguard and snack stand. The water is cooler and waves rougher and once again, the shark flag was flying.

That evening we traded dinner shifts with my parents. They went for an early dinner at Twenty-Eight Atlantic in Harwich and then we went for a late dinner on the veranda at Chatham Bars Inn. Unfortunately, it was already dark and a heavy fog had rolled in so we didn’t get to experience the view but the food was delicious – we especially loved the Chatham Raw Oysters and Creste Di Gallo pasta. We played much of the week by ear and failed to make any reservations ahead of time so this was perfect since the veranda is first come, first serve and the hotel offers free valet parking.

August 21, 2021 – Travel Day [Chatham – Buffalo]

Saturday morning, we cleaned up the house, packed up the cars and were off. We did get stuck in heavy Saturday traffic on 6 trying to get off the Cape – I think also due in part to tropical storm Henri’s pending arrival the following day but eventually we made our way to interstate 90 and cut through MA and NY before stopping in Buffalo for the night at Holiday Inn Express Cheektowaga North East.

August 22, 2021 – Travel Day [Buffalo – Cleveland – Chicago]

We got a late start the next morning and grabbed a quick bite to eat at the breakfast buffet before getting on the road. On the way home, we stopped in Cleveland to visit with family for a few hours and then eventually arrived back in Chicago around 8:30PM.

Overall, it was an amazing trip! The drive from Chicago was LONG but it went far better than I ever imaged possible and I’m proud of us for making this trip happen because the memories we made are priceless!

Accommodations & State Specific Details

Airbnb Chatham Get Away

We knew we wanted to stay in Chatham but had a difficult time finding any reasonably priced rentals for our dates. Then this two bedroom, one bathroom house popped up on Airbnb and it was the perfect size for our group. We ended up sharing it with my parents and it was a bit tricky sharing a room with two babies but we made it work.

Overall, it’s a charming and simple little house. It is clean, the air conditioning is strong and it comes with some great amenities including a grill, outdoor patio, updated kitchen, beach chairs and washer/dryer. It also has a screened in porch that was the perfect place to enjoy a cup of coffee in the morning or a glass of wine post beach.

However, I think my favorite aspect of this house is its location in South Chatham. It’s centrally located on the Cape so we were able to get up to both the Upper and Outer Capes in about 45 minutes. It took us about 10 minutes to drive into downtown Chatham and we could easily walk to Forest Beach, the small local beach.


To Cape Cod: We drove from Chicago! In total it took about 20 hours each way but we broke the drive into two days, stopping in Cleveland on the way there and Buffalo on the way home.

Around Cape Cod: We mostly drove but we were able to walk to Forest Beach which was awesome.

Currency: US Dollar (USD)

Language: English.

Outlet Adapter: The standard voltage is 120 V. The standard frequency is 60 Hz. The power sockets that are used are of type A and B. Standard United States adapters.

Passport/Visa Requirements: No U.S. Passport required.

Vaccinations/Medicines: When we visited Chatham, there was not a COVID mask mandate in place but individual stores/restaurants had different policies.

Weather: We visited Cape Cod in mid-August and the weather was near perfect. The week we were there, the highs were in the upper 70’s / low 80’s and the lows were in the mid-60’s. It rained one day [Thursday] but every other day was sunny with the occasional cloud cover. Evenings and mornings were a bit cooler but still comfortable enough to be outside without additional layers.

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