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A Day Trip to Chatham: Beaches, Main Street, and Cape Cod Charm

Plan the ultimate day trip to Chatham, MA. Explore charming Main Street, visit the iconic Chatham Lighthouse, relax on Lighthouse Beach, and savor fresh seafood. Discover Cape Cod’s coastal charm in just one day.
Chatham Five Star Day Alt text

A Day Trip to Chatham: Beaches, Main Street, and Cape Cod Charm

Quick Itinerary

Morning

  • Breakfast: Start your day at Chatham Filling Station for hearty breakfast plates or grab a quick coffee and pastry at a local café.
  • Explore Main Street: Stroll Main Street, the heart of Chatham, where you’ll find boutique shops, art galleries, and charming local businesses.

HLCC Tip: Visit Main Street early in the morning to enjoy a quieter, more relaxed experience.

Midday

  • Lunch: Enjoy fresh seafood at Mac’s Chatham Fish & Lobster or casual eats at Chatham Squire.
  • Afternoon Activities: Visit Chatham Lighthouse and take a walk along Lighthouse Beach.

HLCC Tip: For a unique perspective, visit Lighthouse Beach at low tide to explore the tidal flats and spot local wildlife.

Evening

  • Dinner: Wrap up your day with a meal at Del Mar Bar & Bistro or Pate’s.
  • Sunset: End your trip with a peaceful sunset at Ridgevale Beach.

HLCC Tip: Bring a blanket and some local snacks for a cozy sunset experience at Ridgevale Beach.

Our concierge team can help you source the best picnic essentials from local markets. Reach out anytime to concierge@hyperlocalcapecod.com.

A Perfect Day in Chatham, MA

Morning: Breakfast and Main Street Stroll

Start your day with breakfast at Chatham Filling Station, a local favorite known for its hearty plates and welcoming atmosphere. If you’re in the mood for something lighter, grab a coffee and pastry from a nearby café before heading to Main Street.

Main Street is the heart of Chatham and offers a quintessential Cape Cod experience. Stroll past boutique shops, art galleries, and charming local businesses. Don’t miss stops like Narrowland Gallery or Artful Hand Gallery to admire local artwork.

HLCC Tip: Visit Main Street early in the morning to enjoy a quieter, more relaxed experience.

Chatham Five Star Day Alt text
Chatham Five Star Day Alt text

Midday: Lunch and Lighthouse Adventures

For lunch, head to Mac’s Chatham Fish & Lobster for fresh seafood or enjoy the lively atmosphere at Chatham Squire, a local institution. Both spots offer delicious meals that capture the flavors of Cape Cod.

After lunch, visit the iconic Chatham Lighthouse, a historic landmark that offers stunning views of the coastline. Take a walk along Lighthouse Beach, one of Chatham’s most picturesque spots.

HLCC Tip: For a unique perspective, visit Lighthouse Beach at low tide to explore the tidal flats and spot local wildlife.

Evening: Dinner and Sunset

End your day with a delicious dinner at Del Mar Bar & Bistro, known for its creative menu and cozy atmosphere, or Pate’s, a classic Cape Cod dining experience.

After dinner, head to Ridgevale Beach to watch the sunset. The calm waters and stunning views make it the perfect way to end your day in Chatham.

HLCC Tip: Bring a blanket and some local snacks for a cozy sunset experience at Ridgevale Beach.

Our concierge team can help you source the best picnic essentials from local markets.

Chatham Five Star Day Alt text

Featured in This Itinerary

A picturesque stack of three blueberry pancakes on a white plate seated on a line-art table cloth. The pancakes are topped with powdered sugar. There's a place setting to the right of the plate and the sun comes in from the right through an unseen window.

Chatham Filling Station

A local favorite for breakfast and lunch, The Chatham Filling Station serves classic diner fare with a coastal twist. Known for its warm atmosphere, this casual spot features items like fluffy pancakes and lobster rolls. One standout menu item is their corned beef hash, often praised for its fresh ingredients. Open year-round, it’s a great spot for a hearty, comforting meal any time of the year​.

Painting of a rocky shoreline and a body of water during sunset. The shore is almost silhouetted but the rocks can be seen. The sky is beautiful shares of orange yellow, and violet reflected nicely in the water. A silhouetted person walks out onto the rocks in the middle of the image.

Narrowland Gallery

Narrowland showcases innovative, edgy works, with a special focus on photography and modern art. Featuring artists such as Christopher Seufert, the gallery is known for its bold and eclectic offerings. Open year-round, Narrowland provides a fresh perspective on the Cape's art scene, blending contemporary photography with other mediums.

A color photo of Main Street in the town of Chatham on a sunny day. The sky is blue. There are some people crossing the street. Tracing the edge of the image is a thin white line that squares itself. Bright pink flowers dot the foreground.

Artful Hand Gallery

This gallery combines fine art and craft, showcasing a wide array of handmade items alongside traditional paintings and sculptures. Visitors will find jewelry, ceramics, and other artisan creations that complement the gallery’s fine art offerings. Artful Hand Gallery is open year-round and is a great place to find unique, handcrafted gifts.

This restaurant's version of a poke bowl - served in a deep white dish. The salmon, tuna, and other fish are clumped together very appetizingly with some garnish on top. There is a bed of white rice underneath.

Mac’s Chatham Fish & Lobster

A part of the well-known Mac’s Seafood family, this market and restaurant is perfect for seafood lovers. Mac’s Chatham Fish & Lobster offers fresh local fish and shellfish, available for both dining in or takeout. Their lobster rolls are especially well-regarded. Along with the seafood counter, they serve cooked seafood dishes like fried clams and fish tacos. Open year-round, it's a must-visit for fresh, sustainable seafood​.

Looking diagonally down the front of a bar/restaurant in the daytime. It's a low slung one-storey place sided with wooden shingles and paned windows looking in and outside. Seafood and alcohol are advertised in printed script on blue painted walls beneath the windows.

Chatham Squire

Chatham Squire is a lively, classic spot in Chatham, offering an old-school tavern vibe with a fun, bustling atmosphere. Known for its hearty seafood dishes, the Chatham Cioppino and fried clams are local favorites. The restaurant also features a bar with live music and a variety of beers and cocktails, making it a great place for both meals and a night out. You'll see an Irish band sitting at a table in the dining room giving a full on concert surrounded by spectrum of people of every age. Sometimes they can get over the age differences, sometimes they can't but everybody has a good time until the uber rolls through. The Squire is open year-round, making it a reliable choice for locals and visitors alike.

A tall white lighthouse is coupled with a barn-style house. It stands at the end of the large grass front yard. Beyond the lighthouse and it's flank barn there is a gorgeous golden red sunset blazing like a fire approaching.

Chatham Lighthouse

A key feature of Chatham’s coastal landscape, the Chatham Lighthouse has stood since 1808, providing a beacon for mariners navigating the treacherous waters off Cape Cod. This working lighthouse offers tours during the summer season, typically on Wednesdays, allowing visitors to climb to the top for panoramic views of the Atlantic Ocean and Monomoy Island. It's an important symbol of Chatham’s maritime heritage, with an informative display on the history of shipwrecks and coastal rescues in the area. The lighthouse is still operated by the U.S. Coast Guard and continues to serve its original purpose while also offering educational insights into the town’s nautical past.

Looking down from the wooden stairs that lead down the sand at a sprawling fine-sand beach. The beach is crowded with beach grass, cutting paths in several direction before the water. The sky is blue with some thin clouds.

Lighthouse Beach

One of Chatham’s most scenic spots, located near the iconic Chatham Lighthouse. This expansive beach offers dramatic views of the Atlantic Ocean and is a favorite for sunbathing and strolling along the shoreline. Due to strong currents, swimming here is limited, but the breathtaking scenery makes up for it. Parking is limited, and there is no designated lot, so visitors often park and walk from nearby streets. Lifeguards are present, and beach fires are not allowed.

An oval shaped white ceramic plate holds a serving of crispy pork belly and glazed potatoes. The herb garnish can be seen on the white of the potatoes and the pork belly cuts are perfectly shaded golden brown colored.

Del Mar Bar & Bistro

Del Mar is known for its inviting atmosphere and upscale yet relaxed vibe, offering a mix of local seafood, bistro dishes, and wood-fired pizzas. One standout item is the Fig & Prosciutto Pizza, highly praised by diners. The restaurant has an extensive wine list and craft cocktails, making it a popular destination for both locals and tourists. They are open for dinner from Tuesday to Saturday and closed on Sundays and Mondays, with reservations highly recommended due to its popularity. It operates year-round​.

A beautifully plated dish: seared tuna perfectly cooked and pink in the center. Served on a bed of sauced edamame & rowe and topped with a mango chutney & diced. herbs. Past this place, on the rest of the white clothed table are two other dishes and several full wine glasses.

Pates

A longstanding Chatham institution, Pates has been serving Cape Cod locals and tourists for over 60 years. Known for its classic American fare, it offers a diverse menu with a focus on prime cuts of steak and fresh seafood. A standout dish is the center-cut boneless New York sirloin, grilled to perfection over an open flame. The restaurant’s old-school charm is enhanced by its comfortable lounge, where guests can enjoy dishes like fried fish and chips or a steak sandwich. Pates is open year-round and provides an authentic Cape Cod dining experience steeped in tradition​.

A sandy beach fills the bottom half of the frame. On the beach closer to the water stands a lifeguard chair and four people hanging out as the sun goes down on the otherwise empty beach. The sand is flanked by tall dune grass on the right. The sky is the top half of the frame and dark blue and yellow.

Ridgevale Beach

One of Chatham's best options for families, with its combination of a large sandy beach and tidal pools that are perfect for children to explore. The beach sits at the meeting point of the ocean and a salt marsh, providing calm, shallow waters suitable for swimming and kayaking. A snack bar and restrooms are available, enhancing its family-friendly appeal. Parking is available with a permit during the summer, and the large lot makes it relatively easy to find a spot, even in peak season. Fires are not permitted on the beach​.

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