Insiders Guide to Chatham, MA

Group photo outdoors with water backdrop, The Scout Guide, smiles, and a check.

While everyone from Bergen County knows that the best beaches on the East Coast are just a few miles down the Garden State Parkway on the Jersey Shore, Co-Editor, Chris Doherty, has the inside scoop on another perfect summer beach getaway, Chatham, Massachusetts.  For more than 40 years, her family has called this quaint town on Cape Cod home for the summer and she is sharing her insider tips with our TSG Bergen County friends.

Getting There:

Beat the traffic: There is no denying it, I95 is always under construction.  The best advice is to hit the road by 6:30am and if possible travel on a weekday.  Plan on the trip taking 5.5 hours.  For a great mid-point break, stop into downtown Stonington, CT and grab a coffee at Indulge Coffee or a waterside meal at The Dog Watch Cafe where your pups are eagerly welcomed.


Jet Blue and American Airlines offer daily flights to Hyannis from JFK and Laguardia.  Or book a private flight to Hyannis with our Scout Guide friends from Aircraft Services Group. Car rentals are easily available at the Hyannis airport, or you can grab an Uber for the 30-minute ride to Chatham.



Chatham has a wide variety of rentals to suit your family’s needs.  We recommend Pine Acres Realty, Pretty Picky Properties and VRBO for some of the best listings.


Chatham Bars Inn: By far, this is the most picturesque and luxurious hotel in Chatham.  This oceanfront resort offers rooms and cottages and their beach, pool, and restaurants are top-shelf. The gazebo bar is a must for sunset cocktails, nightly entertainment, and delicious coal-fired pizzas. 

The Chatham Inn: Located at the top of Main Street, this quaint inn is a Relais Chateaux with a gourmet restaurant.  This hotel is great for couples looking to be near the action but who appreciate a quieter escape.

Wayside Inn: Located on the heart of Main Street, this mid-sized property is great for families or couples looking for a walk-to-everything location.  Their Wild Goose Tavern offers pub favorites and diners enjoy its porch setting.  


TSG Tip: Getting a table anywhere in Chatham is very tough so make reservations as soon as you have your vacation booked.

Bluefins Sushi & Sake Bar: Amazing sushi favorites and Korean Ribs. The restaurant is very small but they do a booming take-out business.  Place your order early in the day so it is ready for you at dinner time.

Del Mar Bar & Bistro: Stylish bistro fare, thin-crust pizzas and seafood specialties.

Chatham Fish Pier:  This shack at the working fish pier on Shore Road has the freshest seafood in town and their menu items are perfect for grab-and-go or eating at one of their picnic tables.  Call ahead and order a complete lobster dinner steamed, cracked, and ready to be picked up for in-home dining at your preferred time.

The Impudent Oyster: We love this spot for dinner at their cozy bar.  The Devils on Horseback and Clams Casino are always our favorite.  

The Chatham Squire: People line up down the block for their late night drinks and live bands.  The casual family-style restaurant offers typical seafood entrees, but you don’t really go to the Squire for a gourmet meal.

TSG TIP: Consider a Private Chef Dinner

Enjoy the most delicious meal in town by hiring The Handsome Oyster to create a gourmet dining experience in your own home. This business is led Wesley Krell, the nephew of our @tsgbergencounty friends Stew and Kris Krell from F.Silverman Jewelers.  Wes will work with your group to create a unique dining experience that surpasses every option in town.

Must Hit Food Shops:

Chatham Candy Manor: Amazing Fudge, chocolate and penny candy selection.

Buffy’s Ice Cream: We love their Black Raspberry Chip Ice Cream and their homemade ice cream sandwich bars.

Snowy Owl Coffee: Hidden down a quaint courtyard behind the Lily Pulitzer shop, folks line up early for the best coffee and lattes in town.

The Chatham Market: This mini food store at the bottom of town has the best muffins and breakfast breads in town.  Their chicken salad is also yummy.

Must-hit Boutiques:

Lola Mer: Relatively new to Chatham, we love the curated collection of fashion in this small, fashion-forward boutique.  The shop is down from the main shopping area, but definitely worth the few extra steps.

Chatham Home: You’ll want to redecorate your entire Bergen County home in a coastal aesthetic once you visit this lovely home furnishing shop. This is a great shop for hostess gifts too.

Mahi Gold: A Chatham original, we have been buying dresses here for years and their prints never go out of style.

Ben Franklin: The original Five and Dime shop is the perfect place to find a rainy day activity or beach gear.

The House of Findings: Stylish Vintage clothing and accessories.

Forest Beach Jewelers: Beautiful, handmade jewelry and charms.


Chatham A’s Baseball: Catch a home game at the stadium in town.  The Cape League is renowned for its top flight college baseball players who are all pro prospects.

Go to the Band Concert: Every summer Friday night at 8:00pm,  enjoy live music at the Chatham bandstand in the center of town.  Lay your blanket out early for the best spot.

Climb the Chatham Light: Climb the 44 winding steps to the top of the lighthouse every Wednesday in July and August.

Fourth of July Parade: Experience the best 4th of July Parade for miles around.  

Outermost Harbor Marine can shuttle you to an outer beach for a pristine beach day.  You will definitely see seals along the way. 

Chatham Seaside Links: Golf along the coast at this in-town, 9-hole, par 3 course. Tee times can be booked two days in advance.

Lighthouse Beach Morning Yoga: Jumpstart your day with morning yoga on Lighthouse Beach with Jennfra Norton. With some planning, Jennfra will host a private session for your group at your home.  

To book your next vacation in Chatham, contact:

Whimsie Luxury Travel / @whimiseluxurytravel

TSG Tip: booking luxury hotels like The Chatham Bars Inn with a travel professional has lots of fringe benefits – we know from experience.

Be sure to follow @tsgbergencounty for more Insiders Guides and TSG tips.