Boston in the Fall: Best Hotels Restaurants and Activities

Boston, Massachusetts, is a truly stunning city, usually pictured with historical architecture and the golden leaves of the Fall season, as such, this makes it a truly perfect time of year to visit!

No matter what you want your cozy Boston trip to look like, here are some of the city's best hotels, restaurants, and activities for you to enjoy.

Best Hotels in Boston

The hotel scene in Boston is incredibly diverse, with many popular hotels being renovations of some of the city's most impressive historic buildings! Many of the hotels on this list guarantee a unique history lesson, alongside a comfortable and cozy stay, with a great range of amenities either on-site, or right on the doorstep, offering a convenient place to stay during your Boston getaway.

From classy, elegant, boutique hotels housed in former jails, to a quirky, music-themed place to stay, the exciting array of hotels in Boston truly offer something for every type of visitor!

The Colonnade Hotel, Back Bay, Boston

Located in downtown Boston, this luxury hotel sits within a short walk of Symphony Hall, the Prudential Center, the Public Garden, Fenway Park, the South End, and just across from Prudential Train Station, making it a great base from where you can explore the city's greatest sights.

Unlike many other outstanding hotels in Boston, this hotel actually boasts a seasonal rooftop pool, which makes it a great choice if you're more flexible with your visits and can visit in late summer rather than during the peak of the fall season. It has boasted an exceptional standard of customer service since its opening in 1971, and to this day, has an amazing concierge service that can help take care of all your travel arrangements. The hotel has a range of great on-site facilities, including a bar and dining options.

This hotel underwent a fabulous renovation in 2020, contrasting modern furniture with stunning floor-to-ceiling glass windows to create a fresh, new look. Each of the spacious rooms boasts a 59-inch flat-screen TV, an iPod docking station, and a Keurig coffee maker.

The Verb Hotel, Fenway-Kenmore, Boston

Located just 656 feet from the popular Fenway Park Stadium, The Verb Hotel sits pride of place, with several great attractions and dining options within close proximity. 

Originally a 1959 motor inn, The Verb has since been restored in a way that pays homage to the building's past, while maintaining contemporary finishes and comforts to guarantee a great stay. With a fun lobby, reminiscent of a recording studio thanks to it's vintage music posters and quirky decor; a heated, outdoor, saltwater pool; and a lively ground-floor Japanese izakaya-style restaurant that's as popular with locals as it is guests, there's plenty on offer at The Verb.

The charming rooms at this hotel each feature air-conditioning, cable TV, and free Wi-Fi access. Pool-view rooms overlook the sundeck that sits at the rear side of the hotel, and the "Backstage Trailer" rooms consist of a line-up of re-furbished Airstream trailers, so you can enjoy a stay where you feel like a true rockstar! 

The Liberty, West End, Boston

Overlooking the Charles River in Boston city center, the former Charles Street Jail was once an eyesore. After opening as The Liberty, a boutique hotel, it became an overnight sensation, inviting guests to enjoy a luxurious stay in a truly great area of Boston. Sitting at the foot of Beacon Hill, in the heart of the city, The Liberty hotel is just mere steps away from the Museum of Science and Kendall Square. The shops at Faneuil Hall and  the historic harbor area are also only moments away.

Originally built back in 1851, before opening as The Liberty Hotel in 2007, this stunning establishment combines the original, historic style and architecture with today's modern conveniences and luxury decor. It boasts a great range of modern amenities, including free Wi-Fi, state-of-the-art fitness facilities, free seasonal bicycle rentals, free seasonal yoga classes, and a great on-site concierge service that can arrange boat and kayak rentals.

The hotel also boasts award-winning dining and lounge options, including modern American cuisine at the popular 'Clink', a selection of unique craft cocktails at 'Alibi', contemporary Italian dishes at 'Scampo', and an extensive wine list down at 'The Liberty Bar'.

This historic landmark hotel boasts luxurious guest rooms, which feature contemporary American design, floor-to-ceiling windows, sweeping views of the river, and flat-screen TVs.

The Revolution Hotel, South End, Boston

Sitting just a 5-minute walk from Back Bay and within 0.9 miles of the city center, there are lots of popular spots near The Revolution Hotel, including Boston Public Garden, Boston Common, and Boston South Station (for getting around the city with ease!).

This former historic YWCA building has had new life breathed into it through its renovations to become The Revolution hotel, and now boasts utilitarian-chic rooms and art-filled community spaces, that make it a quirky place to stay for those looking for a cozy city break. This 3-star hotel boasts complimentary bike rentals so guests can get around the city with ease, an on-site fitness center, a shared lounge, a great restaurant, a business center, a 24-hour Front Desk, an ATM, vending machines, and Free Wi-Fi.

A popular spot with younger travelers looking for a city break thanks to the competitively priced rooms, The Revolution promises stylish value for solo travelers, couples, and duos who choose to stay here. Some of the rooms are so small, thanks to the historic architecture, that this means sharing a bathroom, but if that doesn't sound like your thing, there’s an en-suite, entry-level category that doesn't break the budget! You can also upgrade to the Studio Suites or newly-added Revolution Lofts, which are located next door to the main hotel building.

The Newbury Boston, Back Bay, Boston

Located less than 10 minutes from the City Center and Back Bay, The Newbury Boston is a recently renovated hotel that sits near some of the city's greatest points of interest, including the Boston Public Garden, Boston Common, and Hynes Convention Center.

The Newbury Boston stands as an upmarket 5-star hotel that provides some truly outstanding on-site amenities and facilities, including complimentary bike rental, a garden, a shared lounge, a bar, a 24-hour front desk, and free Wi-Fi.

Guests can enjoy an à la carte breakfast, or indulge in a luxury evening meal at the popular on-site rooftop restaurant Contessa, which books up weeks in advance. The hotel also boasts some great attractions for art lovers, including works of art and homages to some of America’s most iconic creators, such as a portrait of Ernest Hemingway by Yousuf Karsh that hangs right beside the lobby bar!

There are a total of 286 rooms at this hotel, and this includes an astonishing 90 suites - All of which boast a TV and other great amenities. Some of the suites house gorgeous wood-burning fireplaces (birch logs provided), views of the downtown skyline across the park, a kitchenette (equipped with a fridge, a microwave, and a minibar), and a TV, making them a truly cozy spot to cozy up in Boston in the Fall.

Best Restaurants in Boston

When it comes to choosing the perfect place to dine in Boston, there's an abundance of great options. With a great range of both casual and upscale eateries, there's plenty on offer here, especially when you're looking for some delectable comfort food to warm you during the cool Fall season.

Whether you're looking to dine on something new and adventurous, or hoping to try the best of the best when it comes to your favorite dishes, there's a culinary experience for everyone in Boston.

Amar, Back Bay, Boston

A fairly new restaurant to Boston, Amar was originally established by NYC Michelin-starred chef George Mendes, and boasts a gorgeous range of Portuguese cuisine, available in an upscale, elegant setting, on the 17th floor of the luxurious Raffles hotel.

George Mendes has devoted his time to creating classic dishes that he grew up eating, taking the reminiscent flavors of his childhood, and putting his own, unique spin on them.

We highly recommend the pekin duck, where the sauce is poured tableside, but arguably, the true star of the show here is the desserts. The made-to-order pão de ló sponge cake is served alongside smoked cinnamon ice cream, giving it an irresistible autumnal taste.

Krasi, Back Bay, Boston

This chic, Greek wine bar boasts a truly gorgeous selection of off-the-beaten-path meze and fire-grilled souvla, alongside an unmatched wine list that truly compliments the wide array of dishes on offer here.

The name 'Krasi' actually means 'Wine' in Greek, and this restaurant more than lives up to that name! Boasting over 180 natural, organic bottles of wine sourced directly from the Greek Islands, there's a truly unbeatable selection for wine lovers and connoisseurs. The Greek cuisine on offer at this establishment is equally as impressive, spinning creative twists on a selection of traditional dishes, and compiling some of the best Greek flavors for truly unbeatable sharing options.

We highly recommend ordering a selection of dishes to share with the table (it is Mezze style, after all!) Some of the best choices include the halloumi-stuffed tiropita rolls, zesty charcuterie, tzatziki mixed tableside, and the grilled octopus. If you're on the hunt for something truly unique from the wine list to wash this all down with, be sure to sample a glass of orange wine!

Woods Hill Pier 4, South Boston Waterfront, Boston

What better way to recoup from a stroll in the chilly, Fall weather, than to indulge in some hearty, farm-to-table dining, over stunning views of the Seaport waterfront? Boasting modern, seasonal creations, there's something here to suit everyone.

We recommend sampling the pork belly, served with smashed cucumber, cherries, and salsa macha if it's on the menu, or visiting for brunch, where you can enjoy a shellfish platter or lobster popover, right on the waterfront patio.

Brewer's Fork, Charlestown, Boston

This all-day dining spot, located in Charlestown boasts a comforting menu built around wood-fired pizza, savory roasted vegetables, ice-cold local oysters and the one of best selections of craft beer in the city. With some of Boston's best Fall foods on offer it's the perfect spot for family-friendly dining, just off of a picturesque walk.

If time permits, visit for brunch on a weekend, when you can enjoy creative dishes, such as the wood-fried frittata, decadent waffles, and home-made sausages. 

Toro, South End, Boston

Ken Oringer's Spanish tapas restaurant continues to offer one of Boston's most truly outstanding and consistently fun dining experiences, almost two decades since it first opened.

This cozy, industrial eatery always fills up, and it can be tricky to get a table, but the hidden backyard patio is perhaps one of this area's best key secrets - The perfect place to indulge in a culinary adventure before the weather gets too chilly!

Since it's a tapas restaurant, it's a menu made for sharing, meaning there's a huge selection of small dishes to choose from. Some of the best include the quince-glazed smoked duck drumsticks, maíz asado (zesty, saucy grilled corn), and the gambas al ajillo (griddled garlic shrimp)

Best Activities in Boston

Boston is a truly stunning city to visit during the Fall season, and as such, there's a huge range of stunning historical attractions, and beautiful indoor activities to enjoy. Each of which truly helps set the scene for major Fall aesthetics!

From enjoying some of the city's best historical landmarks simply for their design, to taking a peek into their history and culture, there's plenty of great attractions to visit in Boston in the Fall.

Fenway Park, Fenway-Kenmore, Boston

Home to the infamous Boston Red Sox, Fenway Park is one of the most well-known baseball stadiums in the country. Built in 1912, it stands today as both one of the oldest, and one of the most iconic ballparks in Major League Baseball history. Whether you're a fan of baseball or not, this stadium is truly one to be appreciated.

If you won't be visiting while there's a game on, don't worry - You can still see this historical and infamous ballpark via the Fenway Park tour, where you can learn everything there is to know about the stadium and the Red Sox.

Not a fan of sports at all? No worries! Fenway Park also serves as a stadium for large-scale concerts and live music events.

Boston Museum of Fine Arts, Fenway-Kenmore, Boston

The Boston Museum of Fine Arts is one of the most renowned art museums in the world, and it’s easy to see why. Boasting an incredible array of artworks, taken from almost every era and culture imaginable, this vast museum boasts such a great range of exhibits that it's easy to get caught up and spend a whole day here!

Fall in Boston can get pretty rainy, and what better way to spend those rainy days than tucked away inside this colossal, yet cozy, fine arts museum?

One of the most impressive collections housed at this museum is its array of Ancient Egyptian artifacts, including everything from mummies to jewelry - but if a peek into history isn't as much your thing, worry not, as there's plenty to see here for the lovers of modern and contemporary art too!

Salem Witch Museum, Salem

If you're planning on a trip to Boston during the fall season it's almost an unwritten rule to head out the nearby town of Salem for a day. Known all across the world for the Salem Witch trials of 1962, the dark history behind this little town is exactly what put it on the map.

As Halloween rooms and leaves fall from the trees, the Fall season is one of the most picturesque times of year to visit this little town, and more specifically, the Salem Witch Museum.

This museum examines the events of the Salem Witch trials of 1962, where more than 200 people were accused of practicing witchcraft, leading to the execution of 20 of these individuals. If the history surrounding this event intrigues you, be sure to spend some time visiting this museum!

Boston Public Library, Back Bay, Boston

It may surprise you to learn that the Boston Public Library is actually one of the city's most popular destinations. Withstand glass windows, a soaring ceiling, and seemingly never-ending rows of reading lamps, the main reading room is certainly a sight to behold.

Founded in 1848, this iconic landmark has been a key part of Boston's history for over 170 years. Thanks to its spectacular architecture and rich history, it's the best place in the city to cozy up with a good book during the Fall season, and makes a truly spectacular attraction for bookworms!

The library is so extensive that it is actually home to over 23 million items, including a huge range of books, manuscripts, maps, and photographs, alongside tapestries, galleries, statues, and even a stunning courtyard garden with a beautiful fountain.

Quincy Market, Government Center, Boston

The Government Center sits at the heart of Boston, and was designed to be the central location for merchants and traders. As such, this is where you'll find the historic Quincy Market.

Originally opening in 1826, it was one of the first public markets in the United States. Today it is home to a huge selection of shops and restaurants and is a popular destination when it comes to shopping for both locals and tourists. 

So whether you're looking to get your hands on fresh produce, unique gifts, or even a Harvard sweatshirt, this is the place to be! There are even street performers that take place in the square just outside the market, so there's plenty to enjoy while soaking up the atmosphere!