A Guide To The Perfect Weekend in Massachusetts

From the bustling streets of Boston to the laid-back energy of Martha’s Vineyard, Massachusetts has a diverse selection of attractions suitable for travelers of all kinds. The Bay State, as it is often called, is well known for its mouthwatering lobster rolls, Revolutionary War history, and vibrant coastal beaches. Those looking to enjoy a weekend getaway in Massachusetts can explore everything from charming small towns to world-class museums, all while soaking in that classic New England charm that defines the state. So, if you are ready for the perfect weekend trip, check out this ideal Massachusetts itinerary.

Friday: Boston

For a memorable weekend in Massachusetts, the historic city of Boston is a great place to start. Travelers looking for accommodations that highlight the city’s rich historical background can check into the Omni Parker House. The popular hotel was founded in 1855, and in addition to being one of the city’s oldest and most elegant inns, it is also the “longest continuously operating hotel in the United States.”

On the Omni Parker House website, the hotel highlights iconic past guests, including the likes of author Nathaniel Hawthorne, baseball legend Babe Ruth, former president John F. Kennedy, and famous actor Judy Garland, just to name a few. The hotel’s ideal location along Boston’s Freedom Trail makes this a fantastic home base for the rest of the weekend.

The Freedom Trail

After checking into the hotel, it’s time to hit the Freedom Trail. This 2.5-mile red-lined route takes curious visitors past 16 historic sites, including various churches, meeting houses, and state buildings. Some highlights include the Boston Common, Park Street Church, Boston Latin School Site, Old South Meeting House, Boston Massacre Site, Paul Revere House, and Bunker Hill Monument. Along the way, visitors will take in over 250 years of history while being led by 18th-century costumed guides (when available). Alternatively, travelers can choose to take a self-guided tour, stopping to explore select sites that interest them. Those who get hungry along the trail can stop at the popular Quincy Market, the oldest and biggest food hall in the US.

New England Aquarium

Next, head to the New England Aquarium, where fur seals, California sea lions, various penguins, giant Pacific octopuses, weedy seadragons, and thousands of fish species await. The aquarium is open from 9 am until 5 pm daily and offers timed-entry tickets to keep aquarium traffic flowing. In addition to the various exhibits and events hosted here, visitors can also make arrangements to meet and greet select sea animals, such as the Atlantic Harbor Seals. After seeing all the New England Aquarium has to offer, head to Legal Sea Foods for a fresh and tasty seafood dinner. The popular chain restaurant is located just 1.6 miles from the aquarium.

Boston Harbor Cruise

To wrap up your first night in Massachusetts, there is nothing better than a relaxing Boston Harbor Cruise. The boat tour company offers a wide range of excursions, from whale-watching cruises to lively dinner cruises. For this weekend, the Narrated Historic Sunset Cruise is the way to go. The sunset cruise lasts roughly 1.5 hours and offers breathtaking views of the Boston Skyline and the historic Boston Harbor.

Saturday: Salem

From the Omni Parker House, the small charming town of Salem, Massachusetts, is just a short 25 miles away. The town, famous for the 1692 Salem witch trials, is filled with museums and “haunted” historic sites making it an ideal destination for history buffs and Halloween enthusiasts alike.

Salem Witch Museum and Witch City Walking Tour

A trip to Salem is not complete without a stroll through the Salem Witch Museum. The museum features two presentations; the first one details the events of the famous 1692 trials, and the second discusses the meaning behind the word “witch” and how it has evolved over time. From there, travelers can embark on a guided walking tour to experience some of the other historic witch-themed attractions in town. Witch City Walking Tours is a highly regarded tour company that offers a range of witchy-themed tours, each taking roughly 1 to 2 hours to complete. Each tour will highlight different Salem staples, including the Salem Witch Trials Memorial, the Witch House, the Salem Witch Museum, Burying Point, the Bewitched Statue, and filming locations for Disney’s Hocus Pocus, just to name a few.

Salem Maritime National Historic Site

Next, enjoy a different part of Salem’s history at the Salem Maritime National Historic Site. Here, visitors can enjoy views of the Salem waterfront while exploring nine acres of land and admiring twelve historic structures. Notably, the site is “the first National Historic Site in the United States” and helps preserve roughly 600 years of New England's maritime history.

Taste The Beef

When it’s time to break for lunch in Salem, travelers will be spoiled by choice, with everything from American classics to seafood, Mexican food, and more on offer. However, those looking to enjoy something uniquely local will want to get their hands on a famous North Shore-style beef sandwich. Available at several different restaurants in the area, this popular roast beef sandwich is a staple for locals on the North Shore and is characterized by its rare beef, mayonnaise, American cheese, and BBQ sauce. While in Salem, Bill & Bob's Famous Roast Beef is among the best places to try the iconic dish.

Winter Island Park

After filling up on delectable roast beef sandwiches, a stroll through the park is in order. A mere two miles from Bill and Bob’s Famous Roast Beef, travelers will find Winter Island Park. The park sits on a gorgeous 54-acre peninsula and offers travelers the chance to enjoy activities including swimming, fishing, camping, boating, and soaking up the views. Other attractive features at Winter Island Park include a lighthouse and historic forts.

Larcom Theatre

To wrap up the night in Salem, take in a live show at the nearby Larcom Theatre in Beverly, Massachusetts. The Larcom Theatre is a historic location often referred to as "North Shore's hidden gem." Originally built in 1912, the intimate venue seats 600 people and boasts incredible acoustics. Travelers can find everything from theatre and live music to comedy and dance performances.

Sunday: Worcester

A vibrant arts scene and gorgeous outdoor areas come together to make Worcester, Massachusetts a must-visit destination. Located roughly 65 miles from Salem, this bustling city has so many fun things to see and do that it would be impossible to fit them all into one day.

Breakfast at Altea’s Eatery

Before hitting the town in Worcester, fuel up for the day at Miss Worcester Diner. The historic diner has roots dating back to the 1930s and is widely regarded as “the best diner in Worcester.” Inside, diner patrons will find a classic maximalist diner style and a menu filled with mouth-watering items, including various eggs benedicts, omelets, and traditional breakfast plates.

Worcester Art Museum and Museum of Worcester

After breakfast, dive into art and history at some of the city’s best museums. The Worcester Art Museum is open on Sundays from 10 am until 4 pm and features a wide selection of exhibits, events, and 5,000 years of art. The Museum of Worcester is also open from 10 am to 4 pm on Sundays and has roots dating back to 1875 when it was called the Worcester Society of Antiquity. Here, visitors can embark on guided tours and learn about the innovators, workers, and investors of Worcester.

Quinsigamond State Park

Next, it’s time to spend a few relaxing hours surrounded by nature. There are a handful of lovely parks in Worcester, but none quite as appealing as Quinsigamond State Park. The state park is divided into two distinct areas: Lake Park and The Regatta Point. At the Lake Park area, visitors can enjoy swimming at the beach, picnicking, and tennis. At The Regatta Point, activities, including swimming, sailing, picnicking, and fishing, are all available.

Wander on Water Street

Wrap up your Massachusetts adventure by wandering around Water Street in Worcester. The popular street is historically known as a vibrant and tight-knit Jewish settlement, which is lined with bakeries and delicatessens. Today, visitors will find a wide range of bars, restaurants, and the beloved Canal District. Grab delicious Middle Eastern food at the Baystate Cafe & Market, then purchase sweets for the ride home at The Queen’s Cups.

Regardless of where you choose to go, a weekend in Massachusetts is certain to be filled with history, mouth-watering meals, art, and stunning nature scenes. Big popular cities like Boston and Worcester offer endless activities, while small towns, including Salem and Beverly, provide visitors with that classic New England charm. From history buffs to foodies to art enthusiasts, there is a little something for everyone in the Bay State.