TOP 10 Best Ma historic destinations in Chatham, Massachusetts

The Chatham Orpheum Theater is a historic movie theater located at 637 Main Street in Chatham, Massachusetts. This charming venue offers a unique movie-going experience with a mix of classic and contemporary films for all ages to enjoy. With its cozy atmosphere and state-of-the-art technology, the Chatham Orpheum Theater is the perfect place to escape and immerse yourself in the magic of cinema. Whether you're a local resident or visiting from out of town, this theater is a must-visit destination for film enthusiasts.

Chatham Lighthouse, located at 37 Main Street in Chatham, Massachusetts, is a historic landmark and popular tourist attraction. This iconic lighthouse offers stunning views of the Atlantic Ocean and is a must-visit destination for visitors to the Cape Cod area. The lighthouse has a rich history dating back to the early 19th century and continues to serve as a beacon of light for ships navigating the waters off the coast of Massachusetts. Visitors can explore the grounds, learn about the lighthouse's fascinating past, and take in the picturesque scenery that surrounds this beloved institution.

Located at 512 Main Street in Chatham, Massachusetts, the Chatham Wayside Inn is a unique lodging option that combines a contemporary feel with exceptional service. This boutique hotel offers a restful retreat with amenities such as a heated pool and fitness center. Each room and suite has been carefully restored and offers a different look, with spacious rooms and upscale amenities. Guests can relax on the patio or private balcony and enjoy the sea air. The hotel staff, who are locals, are happy to share their knowledge of the historic town and nearby attractions. Special packages, such as the Birthday & Anniversary package and the Month of Love Package, offer guests the opportunity to enhance their stay with added perks. Don't miss out on the Leap Into Savings promotion, which includes savings of up to 15% and a $50 Food and Beverage credit. Whether you're visiting in the spring, summer, fall, or winter, the Chatham Wayside Inn has something to offer for every season. Book your stay now and experience the charm of this historic hotel in Cape Cod.

The Captain Freeman Inn, located at 15 Breakwater Road in Brewster, Massachusetts, is a beautifully restored Sea Captain's mansion just a short walk away from Breakwater Beach. This award-winning Bed and Breakfast has been recognized with the Tripadvisor Certificate of Excellence for the past 11 years, offering guests a deluxe seaside experience year-round. Guests can enjoy the outdoor heated salt water swimming pool and custom firepit, providing the ultimate in luxury and relaxation in every season. The inn also offers a gourmet three-course breakfast made with farm-to-table ingredients, served in a charming indoor dining area or on the screened porch.

Maps of Antiquity is a unique institution located at 1409 Main Street in Chatham, Massachusetts, United States. This establishment is a combination of an art gallery, home goods store, and store, specializing in vintage and antique maps. With a wide selection of beautifully preserved maps from different eras and regions, Maps of Antiquity offers a fascinating glimpse into the past and a perfect way to add a touch of history to your home decor. Whether you are a history buff, a collector, or simply looking for a one-of-a-kind piece, Maps of Antiquity is a must-visit destination for those who appreciate the beauty and significance of antique maps.

Welcome to The North End – Italian Neighborhood, your ultimate guide to experiencing the vibrant heart of Boston’s “Little Italy.” Nestled at 14 North Square in Boston, Massachusetts, this charming enclave is a captivating blend of rich history, diverse culture, and exquisite cuisine. Whether you're a local or a visitor, The North End offers a delightful journey through time and taste. Discover the allure of the North End, one of Boston's oldest residential areas, where the echoes of early European settlers mingle with the lively spirit of Italian immigrants. As you stroll through its narrow streets, you'll be greeted by rustic Italian street signs and the irresistible aroma of authentic Italian cuisine emanating from over 100 restaurants, cafés, and bakeries. From traditional dishes to innovative culinary delights, the North End is a paradise for food lovers.

Nauset Rental is a real estate and travel agency located at 56 Main Street in Orleans, Massachusetts. Specializing in Lower and Mid Cape Rentals in towns such as Orleans, Chatham, Harwich, Brewster, and Dennis, Nauset Rental offers secure online payments, damage and travel insurance, and is locally owned and operated with proper licensing and insurance. Guests have raved about their experiences at Nauset Rental properties, praising the beautiful locations, amenities such as games and music systems, and the excellent customer service provided by owner Kent. With private beach access and stunning views, guests have enjoyed the peaceful and secluded atmosphere of the neighborhoods while still being close to activities and attractions.

Nauset Rental is a real estate and travel agency located at 3 Main Street in Eastham, Massachusetts. Specializing in Lower and Mid Cape Rentals in towns such as Orleans, Chatham, Harwich, Brewster, and Dennis, Nauset Rental offers secure online payments, damage and travel insurance, and is locally owned and operated with proper licensing and insurance. Guests have raved about their experiences staying at Nauset Rental properties, praising the lovely houses and locations, short walks to beautiful beaches, and amenities such as games and music systems. The owner, Kent, has been described as a joy to work with, accommodating last-minute bookings and even welcoming guests with pets. The properties offer private beach access, stunning views, and a quiet, secluded neighborhood close to activities.

Stage Harbor Lighthouse is a historic landmark located in Chatham, Massachusetts, United States. This picturesque lighthouse sits at the entrance of Stage Harbor and has been guiding ships safely to shore for over a century. Visitors can admire the stunning views of the ocean and surrounding coastline from this iconic structure. The lighthouse is a popular destination for tourists and history buffs alike, offering a glimpse into the maritime heritage of the region. Come explore Stage Harbor Lighthouse and experience the beauty and charm of this New England treasure.

The Priscilla House is a charming lodging establishment located at 388 Main Street in the picturesque town of Chatham, Massachusetts. This historic house offers a cozy and welcoming atmosphere for guests to relax and unwind during their stay on Cape Cod. With comfortable accommodations and a convenient location near local attractions and amenities, The Priscilla House is the perfect choice for a memorable getaway in the United States.

The True North House is a charming lodging institution located at 86 Highland Avenue in the picturesque town of Chatham, Massachusetts. Situated in the heart of the United States' Cape Cod region, this cozy retreat offers guests a peaceful and relaxing atmosphere to unwind and recharge. With comfortable accommodations and personalized service, The True North House is the perfect destination for those seeking a tranquil getaway by the sea. Immerse yourself in the beauty of Cape Cod and experience true hospitality at The True North House.

Son of a Sailor, LLC. is a travel agency located at 80 Bridge Street in the charming town of Chatham, Massachusetts. Specializing in creating unforgettable travel experiences, Son of a Sailor offers personalized services to help clients plan their dream vacations. Whether you're looking to explore the historic sights of New England or relax on the beautiful beaches of Cape Cod, the team at Son of a Sailor is dedicated to making your travel dreams a reality. Visit us today and let us help you plan your next adventure!

Welcome to Leroy Anderson Square Located at the historic intersection of Crawford and Chatham Streets in Cambridge, Massachusetts, Leroy Anderson Square stands as a tribute to one of America’s most celebrated composers of light orchestral music. Officially dedicated on May 31, 2003, this charming square commemorates the legacy of Leroy Anderson, whose boyhood home is just across the street at 12 Chatham Street.