Weekend Escapes from Falmouth, MA
Expert Travel Guide by Kerrie Marzot | Discover the Best of New England Within Easy Reach
Nestled on Cape Cod's southwestern tip, Falmouth is the perfect launching point for unforgettable weekend adventures. As a New England travel expert who's visited these destinations countless times, I'm sharing my personal favorites and insider tips to help you plan the perfect getaway.
Nantucket Island
Step back in time on this pristine island where cobblestone streets, historic whaling captains' homes, and rose-covered cottages create an enchanting atmosphere. Nantucket offers breathtaking beaches, upscale dining, and a rich maritime history.
- Whaling Museum & historic district
- Bike the island's 35+ mile path network
- Surfside Beach & Madaket sunset views
- Cobblestone shopping on Main Street
- Sankaty Head Lighthouse
- Cisco Brewers for local craft beverages
Having visited Nantucket in every season, I recommend late spring or early fall for the best experience - you'll avoid the peak summer crowds while still enjoying beautiful weather.
Martha's Vineyard
A diverse island with dramatic cliffs, charming gingerbread cottages, and distinct towns each offering unique experiences. From the vibrant harbor of Oak Bluffs to the historic elegance of Edgartown, the Vineyard captivates visitors.
- Colorful Gingerbread Cottages in Oak Bluffs
- Aquinnah Cliffs & Gay Head Lighthouse
- Edgartown's historic whaling homes
- South Beach & Lucy Vincent Beach
- Vineyard Haven shopping & dining
- Chappaquiddick Island exploration
My personal favorite is visiting the Aquinnah Cliffs at sunset - the colors are absolutely spectacular. For a unique experience, take the short ferry to Chappaquiddick and explore the pristine beaches.
Newport, Rhode Island
Experience the Gilded Age opulence of America's wealthiest families in this historic coastal city famous for its magnificent mansions and world-class sailing heritage. Newport seamlessly blends history with modern coastal charm.
- The Breakers & other historic mansions
- Cliff Walk coastal path with ocean views
- Thames Street shopping & dining
- International Tennis Hall of Fame
- Newport Harbor sailing tours
- Fort Adams State Park exploration
After visiting Newport dozens of times, I've found that the Cliff Walk is most enjoyable early in the morning before the crowds arrive. The mansions are stunning, but don't miss the smaller, more intimate properties like Chepstow.
Providence, Rhode Island
A creative capital with renowned restaurants, vibrant arts scene, and historic New England charm along the Providence River. Home to prestigious universities and a thriving food scene that rivals larger cities.
- WaterFire art installation on select evenings
- Brown University & RISD campus tours
- Federal Hill's authentic Italian cuisine
- RISD Museum of Art collections
- Providence Performing Arts Center
- Riverwalk along Waterplace Park
Having lived near Providence for years, I can attest that the food scene here is exceptional. Federal Hill offers incredible Italian cuisine, but don't overlook the emerging culinary spots in the West End and Downtown.
Portland, Maine
A food lover's paradise with a vibrant arts scene, historic architecture, and stunning coastal views in Maine's largest city. Portland's working waterfront, craft beer scene, and innovative restaurants make it a must-visit destination.
- Old Port district shops & cobblestone streets
- Lobster boat tours & whale watching
- Portland Museum of Art collections
- Local craft beer at 25+ breweries
- Portland Head Light in Cape Elizabeth
- Food tours through the culinary scene
As a frequent visitor to Portland's food scene, I recommend making reservations at least two weeks in advance for popular restaurants. My personal favorites include Eventide Oyster Co. and Duckfat for their incredible takes on New England classics.
Boston, Massachusetts
Immerse yourself in American history, world-class museums, and vibrant neighborhoods in New England's largest city. Boston seamlessly blends revolutionary history with modern urban energy, creating an unforgettable urban experience.
- Freedom Trail historic walking tour
- Faneuil Hall Marketplace & Quincy Market
- Museum of Fine Arts & Isabella Stewart Gardner
- Boston Common & Public Garden
- North End Italian cuisine & cannoli
- Fenway Park tour or game
Having explored Boston extensively, I recommend starting your Freedom Trail walk early to avoid crowds. The North End is my favorite neighborhood - be sure to visit Mike's Pastry and Modern Pastry to decide which has the better cannoli (it's a friendly local debate!).
Seasonal Recommendations
Newport's mansion gardens in full bloom. Perfect for walking tours before summer crowds arrive. Coastal drives with mild weather and blooming landscapes.
Island escapes to Nantucket and Martha's Vineyard. Book ferries and accommodations early. Beach days, sailing, and coastal dining at their finest.
Portland for foliage and harvest festivals. Drive along coastal Route 1 for stunning colors. Fewer crowds and pleasant temperatures for exploration.
Boston's holiday markets and museums. Providence's WaterFire winter lighting events. Cozy coastal towns with festive decorations and fewer tourists.
Weekend Trip Planning Tips
Timing & Reservations
Book ferries 2-3 months in advance for summer weekends. Hotel reservations should be made 4-6 months early for popular destinations. Consider shoulder seasons for better availability and rates.
Transportation
Consider alternative transportation to avoid parking hassles. Many destinations are walkable or have good public transit. For islands, plan how you'll get around once you arrive.
Packing Smart
New England weather can change quickly. Pack layers and always include rain gear, regardless of forecast. Comfortable walking shoes are essential for exploring these destinations.
Budget Considerations
Island destinations are more expensive. Consider shoulder season visits or weekday trips to save on accommodations. Look for package deals that include ferries and lodging.
