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An Off-Season, Safe Trip to Chatham, Massachusetts

By March 23, 2021April 6th, 20214 Comments

Please Adhere To Local Regulations When Traveling Currently In 2021. In Fact, We Urge You To Do Your Part By Staying Home Whenever Possible! Avoid Travel Even If It’s Permitted, And Eventually Get Vaccinated To Keep Our Global Community Safe!

The quiet calm of morning enveloped by a gentle snowfall and steaming cup of coffee is something really magical to experience on Cape Cod. Most people might think of sandy beach days and lobster rolls when planning a trip to ‘the Cape’, but in the wintertime, it’s charm is just as wonderful. Not to mention, you can skip the long lines at the seafood shacks and crowds on the shore to simply take in the views, oftentimes in solitude along the dunes.

We’re big fans of off-season travels. There’s countless perks to travel to ‘warm’ destinations in the wintertime from friendlier fares to less crowds. Some of my most fond adventures are checking out theme parks right after school vacation is over or enjoying some time in rainy London after the holidays.


Of course the winter is lovely on Cape Cod, but I bet many of you are looking toward the summer too and cautiously stepping back into getaway planning. If you’re not ready to share hotel pools though, vacation homes are the ideal choice for Cape Cod, as you can travel with friends and family safely while indulging all the perks of a summer home. Specifically, look to the town of Chatham; it quickly became our ideal spot!

Where to Stay in Chatham as a Group

Chatham falls right in the crook of the elbow of the Cape, about an hour from the canal bridge. A quintessential, walkable ‘downtown’ area is brimming with little shops, restaurants, and a few curiosities to poke around in. The beach is never far away, so we really enjoyed our gorgeous, breezy vacation home that’s only a block or two from the main street.

You can invite up to 11 (!) more guests to come stay with you at this home. With the setup, it’s best utilized by a fun group of friends who don’t mind sharing bedrooms, or two families with a range of kiddos that can have fun in bunk beds and even the crib by the master bedroom. There’s two living rooms areas if you’d like a quiet and rowdier space to hang, plus three full baths and a luxurious jacuzzi tub that overlooks the harbor. 

Take advantage of the outdoor lounging areas by the water and steps accessing the boats too. If you do travel in the warmer season, you’ll love the central AC. And if you’re trying out that digital nomad lifestyle, there’s plenty of space to work at the kitchen table, dining room, and small office off the living room.

If your group is less than a dozen and you’d like to be closer to the shore, there’s another idyllic home situated just steps from Hastings Beach. This property sleeps eight guests with three bedrooms and two bathrooms. There’s also multiple sitting areas with chic nautical decor, a cute kitchen, and lots of outdoor space, including a deck and grill. Downtown Chatham is still not too far away, but the beach is super close for daytime jaunts and plenty of swimming opportunities. 

While we cautiously step back into the light and dream of traveling again, a great way to ease into the idea of a new environment are these two home-y options that undergo rigorous cleaning protocol and are exclusive to you during your stay.

PS, here’s both properties on Airbnb as well if you rather reserve your trip that way, but we are really digging the choices of VRBO for our personal rentals these days!

Outdoors any time of year

If coming from your getaway rentals, Harding Beach is an ideal base for an off-season stroll or a day on the sand in the summertime. There’s lots of space for games and simply soaking up the view. There’s also plenty of parking if you choose to drive.

While out walking, enjoying the beach or driving, it’s worth stopping at the scenic Chatham Lighthouse — it’s nearly a century old.

If you’re staying as safe as possible and just want to get out of the house, there’s a nice drive around the Chatham ‘loop’ to pass all the historic landmarks, pretty shops and main street.

This summer, you can catch some outdoor live music at the Katie Gould park in a variety of genres. Find your new favorite band or even learn a folk dance while mingling with locals and visitors alike.


Chatham’s top eats and activities

We kept a lot of our dining fairly casual this trip, due to our new infant and avoiding busy restaurants (for now). But this did lead us to takeout with the Talkative Pig! My husband claimed it was honestly some of the best pizza he’s had in the US.

Another night we opted for some Caribbean fare, which was also delicious. Branches Grill and Cafe offered amazing takeout, including fried cod, jerk chicken and goat curry with all the fixings.

In the mornings, we’d make coffee, but then go for a second brew at the Chatham Village Cafe and Bakery. Treats such as scones, fritters, and their famous tiger tail donuts are fantastic to treat yourself before a day out on the town.

Of course, if you’re looking to get that homemade clam chowder or lobster roll fix, the Chatham Fish and Lobster Co. or the Chatham Fish Pier are wonderful, seasonal options.

Next time we go to Chatham, I’d like to take a peek at the Shark Center, known for its fun, educational exhibits and commitment to conservation of local shark populations. There’s a few historic museums in town featuring railway artifacts, artwork, and colonial replicas from Cape Cod’s past.

Fun to find just outside Chatham

Take a little drive from downtown Chatham to spice up your early cuisine routine. We loved starting mornings with treats from Hot Chocolate Sparrow in Orleans. This spot is a retro cafe with a large variety of drinks and sandwiches. Not to mention, there’s a huge candy supply and homemade cakes on the menu every day if you really want to indulge. This winter they set up some outdoor heaters and a walk-up window for orders, making a safe and friendly option for food.

Further “down the Cape” is the Cape Cod National Seashore. Obviously it’s full of beautiful beaches, but visitors can also try some seaside hiking, canoeing, fishing, swimming, and even whale/wildlife watching. There’s a half dozen beaches with options for on-sand driving, accessible/wheelchair-friendly visits and plenty of picnics.

If you plan to go to Cape Cod in the near future and are curious about current restrictions, openings and safety precautions, you can use Reopening Cape Cod for the latest news.

Eileen Cotter Wright

Author Eileen Cotter Wright

Eileen Cotter is a freelance travel journalist and owner of Pure Wander. She's our resident expat extraordinaire and falls down a lot in yoga class. Follow her on Instagram @Pure_Wander.

More posts by Eileen Cotter Wright

Join the discussion 4 Comments

  • Andi says:

    I am DEFINITELY an off-season traveler, my hubby and I don’t mind cold, gloomy weather at all and have enjoyed many, many places that were completely empty! It is the best way to go!

  • Pissed off says:

    Writing a guide to encourage people to visit a high risk population during a pandemic…. Well I guess your grandparents don’t live here.

    • I’m so sorry you got that impression! We went on this trip after going absolutely nowhere for more than a year, not even grocery stores, to keep our community and loved ones safe. In the article, I explain how we went to no stores and only got takeout food, bringing much of our own groceries. We drove to Chatham and did not stop anywhere. We did not interact with any other human being while there, exposing no one. Many people will be vaccinated this spring/summer/fall (including myself, fully vaccinated!) so after more than a year of NOT promoting travel, I decided to highlight a contactless holiday rental option. Many travel writers are literally on planes and partying, so it saddens me you felt I haven’t been safe, when it’s my #1 priority.

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