Home | News & Updates | A Seasonal Guide for a Getaway Weekend in Boston

A Seasonal Guide for a Getaway Weekend in Boston


One of the best parts about living in New England is that we are just hours from some of the most popular tourist towns in the country. Portland, New York, and Boston are all within driving distance, making a weekend getaway a must for the summer.

But no matter the season, one city always seems to have something in store that everyone will enjoy. Which city is that?


After all, it was named the 2018 #1 summer vacation spot by U.S. News & World Report. And with Concord Coach’s frequent service to South Station, it’s never been easier and more convenient to get there.

While Beantown and its many options for museums, breweries, shopping, and dining can be overwhelming, we’ve done the hard work for you. Here is a quick seasonal guide for things to do during your weekend in Boston.

Summer in Boston

To kick off the season of fireworks, hotdogs, and the Fourth of July, there’s no better place to visit than right where it all started.

Friday Evening

There is arguably nothing better than Fenway Park on a summer Friday night. The weekend is upon us, it’s a warm summer evening, and the boys of summer are defending their World Series Championship.

Depending on what time you get into the city, we recommend dropping your luggage at the hotel and making your way over to the Fenway neighborhood well before game time. There are countless food and drink options near the park, but they do tend to get busy as you get closer to first pitch. Some of our favorites include:

  • Cask & Flagon: Rated the number two baseball bar in America, this is a great place to grab a bite, a beer, and take in the sights and sounds of the Fenway faithful.
  • Boston Beer Works: Right across from the entrance to Jersey Street (more on that in a minute), this New England chain has one of the larger selections of specialty brews near the park.
  • The Bleacher Bar: This Lansdowne Street legend offers one of the coolest features of any eatery in the area – a view inside the park. The bar is, as the name implies, located beneath the bleachers of the stadium, letting patrons feel part of the action.

If those aren’t really your scene or you have the family in tow, Jersey Street (formerly Yawkey Way) is an awesome, family-friendly pregame destination everyone should experience at least once. You’ll often find Wally, photographers, stilted baseball players various ballpark eats, and more all on this legendary Boston street.


It’s time to get the day started! Rather than eat up valuable hours at a sit-down breakfast, there are a couple grab-and-go options that are practically gourmet.

  • Pavement: This bagel and coffee joint has eight locations throughout the city, and offers a huge variety of pastries, bagels, breakfast sandwiches, and gluten-free/vegan/vegetarian options. They roast their own beans and bake all their own bagels. We are partial to The Fix, a sausage, egg, smoked gouda, and spicy pepper jam sammy on a biscuit. For the vegan visitors, the Vegan Tequila, consisting of seasoned tempeh, diablo tofu spread, pico de gallo, and sprouts served on a bagel, is an equally delicious choice.
  • Boston Public Market: A more out-of-the-box option is the Boston Public Market, a year-round marketplace that brings together over 40 New England vendors selling locally sourced fresh produce and goodies that will satisfy any palate. Some of the best breakfast options include:
    • Union Square Donuts
    • The Popover Lady
    • Levend Bagelry
    • Finesse Pastries

Once you’re full of fresh baked goods and are slightly caffeinated, it’s time to start exploring the city. A day in Boston will look very different for families vs. adults-only, so we’ll break up the options based on your travel companions.


One of the best places to start is at Boston Common and the Boston Public Garden, the oldest park in the country. Located on the Freedom Trail, the Common is always buzzing with locals and tourists alike, taking in the cityscape and enjoying a day in the sun. Just walking the park and finding its many statues and monuments can be fun, but there are a few must-see places.

In case of inclement weather, the Boston Duck Boat Tours are a great way to see the city, and stay dry. With three departure locations at some of the more popular family-friendly attractions, the Duck Boat Tour makes a great launch point for your day in Boston. Tours depart from:



A sunny summer day in Boston is a great opportunity to explore the city on foot, or aboard one of the new Lime scooters scattered throughout the city. We recommend making your way through Boston Common toward Newbury Street, where you’ll find some of the finest shopping in Beantown. Along this route is the Prudential, known as the Pru, which offers some of the best views of the city at The Skywalk.

Once you’ve shopped ‘til you drop, a popular spot to just hang out, listen to music, and enjoy the afternoon is the Lawn on D. Located just a few blocks from the waterfront, Lawn on D is a 2.7-acre outdoor event space that hosts various public and private events, on a rare green space within the confines of the city.

Saturday Evening

A full day out and about in the city will certainly tucker you out, but some of the best dining institutions in the country can be found in Boston – you don’t want to miss out.

Summertime in New England calls for one thing: seafood. Union Oyster House is a famous stop near Faneuil Hall and is the oldest continuously operating restaurant in the United States (established in 1826). For a quicker, more authentic New England option, make your way over to Yankee Lobster Co. Run by a family of lobstermen who have been in the business for nearly 100 years, you can’t go wrong at this Seaport classic.


You have to start your Sunday in the city with brunch. Boston has countless options, some more budget-friendly than others. No matter where you end up, one of the stops on our list will surely appease any appetite.

  • Table Boston: This family-style restaurant only offers one, 11 am seating, creating an air of exclusivity and thus high demand. The food is worth the wait though, as you and your group are served massive plates of breakfast flatbread, omelet tacos, chicken and waffles, and more.
  • Lincoln Tavern: A South Boston staple, Lincoln Tavern actually serves brunch seven days a week, and they were recently named the best brunch in the city. Some local favorites include Fruity Pebble Pancakes, short rib poutine, and smoked salmon eggs benedict.
  • Row 34: What’s better than a lobster roll for breakfast? Probably nothing, but if that doesn’t appeal to you, this Seaport seafood destination has many other incredible options. The brioche French toast with caramel banana and hazelnuts, or the Salmon Gravlax Toast topped with avocado and a sunnyside egg are both delectable options.

Depending on your departure time, a lazy Sunday afternoon is well spent moseying around Quincy Market and Faneuil Hall. You can check out a couple of the shops, or just enjoy the sights and sounds of a beautiful day.

If you’re looking to pack absolutely everything into your weekend in Boston, we recommend visiting one of the many museums this city has to offer. Aside from the Museum of Science and the Aquarium, we recommend the John F. Kennedy Presidential Library, the Isabella Stewart Gardner Museum, or the Museum of Fine Art. If you’re looking to still get in some outdoor fun, the Freedom Trail is a cool way to see the city on foot and learn about our Revolutionary War history.

Summertime Special Events

We would be remiss if we didn’t mention some of the awesome seasonal festivals and celebrations that happen in Boston during the summer. Locals and tourists alike flock to the city for these special occasions, celebrating food, fun, and this wonderful city.

  • Boston Seafood Festival: Held in early August, at the historic Boston Fish Pier, this legendary smorgasbord brings together some of the best local foods, chefs, and entertainment for a day full of, you guessed it, seafood. Eat your way around the pier, watch chef demos, take part in a clambake, and enjoy one of the best Sundays of the summer in Boston.
  • Fourth of July: Notoriously busy, the Fourth of July in Boston is an all-day celebration of our nation’s independence in one of our original cities. The entire city comes alive and the list of attractions and things to do is endless. You might want to try and catch the sold-out Boston Pops, but definitely see the fireworks display over the Charles River, which can be viewed from many vantage points throughout the city.
  • Boston Dragon Boat Festival: The first race of its kind in the United States, the Boston Dragon Boat Festival brings together tens of thousands of competitors and spectators for a fun-filled day on the water. Held in June, teams from across the country come together to race specially designed boats down the Charles.

Autumn in Beantown

Most people associate autumn in New England with weekend getaways to Vermont or New Hampshire, but did you know that Boston has lots going on during this season? The temperatures are just right, foliage is in peak, and you won’t be disappointed with a mini autumn vacation to Beantown.

Friday Evening

Boston is home to some of the best breweries in the country, and a Friday evening is the perfect time to check them out. Not only do many of these breweries have autumn-themed events (more on that later), but a nice New England brew might be the best way to kick off the weekend.

  • Harpoon: Rated the best brewery in the city on Yelp!, Harpoon offers tours, small bites, and has a massive beer hall with plenty of room for you and your friends to enjoy a beer or two.
  • Boston Brewery Taproom: This is the home of Sam Adams lager, one of the more famous Boston beers. The taproom has rotating taps of classic Sam favorites, as well as experimental brews that don’t necessarily go to market.
  • Nightshift Brewing: Their original location was in Everett, but the newest Nightshift at Lovejoy Wharf is the place to be. It has 30 rotating beers, experimental brews, a scratch kitchen, and specialty coffee bar.
  • Trillium: Their prime location is at Fort Point, and Trillium has tastings, tours, and an outdoor patio area for you to enjoy. There is also a full menu and rooftop terrace, so Trillium has a little bit of everything.


One of Boston’s nicknames is America’s Walking City, and a beautiful fall day is the perfect opportunity to take advantage of it.

Start with Freedom Trail, which you can likely pick up wherever you are staying. This 2.5-mile trek takes you along the city’s most famous and historic sites, from the Old North Church to the site of the Boston Massacre. You can sign up for a guided tour or just mosey along the path yourself. No matter what you choose, there are plenty of places along the way to stop and grab a bite to eat or learn more about our nation’s history.

Another great outdoor option is the Arnold Arboretum at Harvard University. This 281-acre escape is full of native wildlife and plants, has tour options or you can opt for a self-guided tour using an app on your phone. Autumn is one of the most beautiful times of year to get outdoors, and the Arnold Arboretum is the perfect opportunity.

Lastly, Allandale Farm is home to Boston’s “last working farm,” where you can check out their farm stand and greenhouse before retreating back to the concrete jungle. Be sure to check out their events page, as they have many rotating and seasonal events you won’t want to miss.

Saturday Evening

A Saturday evening in Boston is a perfect time to check out one of the city’s many music venues that aren’t the TD Garden. The city’s smaller music scene is a alive and well, and there are many venues that charge minimal to no admission fees to see good music. Of course, there are also the larger venues that require tickets, but some are still available at the door.

  • The Middle East: The home to Boston’s rock scene, The Middle East has five adjacent dining and music venues right in Central Square in Cambridge.
  • The Sinclair: Head to Cambridge and you’ll find The Sinclair, an eatery/concert venue backed by The Bowery brings in varying acts from around the country.
  • Paradise Rock Club: This venue is located right next to Boston University, so it can be a bit of young crowd, but this relatively small venue brings in some big names.
  • House of Blues: Yes, this is a chain, but House of Blues Boston has a ton of options. There are multiple stages within the venue, and they book a wide variety of acts, so it’s at least worth checking out.
  • Loretta’s Last Call: This country bar in the shadows of Fenway has live music every night, and will sometimes book some big-time acts. Loretta’s is one of the only spots in the city to hear local country talent.


Sunday is the day to get to anything you couldn’t fit into Saturday. During the fall in Boston, that’s likely a long list. Whether it was a museum, restaurant, or tour, Sundays offer the perfect opportunity to wrap up your vacation.

  • Museum Options: MFA, the New England Aquarium, John. F. Kennedy Presidential Library, Harvard Museum of Natural Science, or the Isabella Stewart Gardner Museum.
  • Restaurant Options: Regina Pizzeria, Neptune Oyster, Caffe Vittoria, L Street Tavern, Parker’s Restaurant, The Tam, or Mike’s Pastry.
  • Tour Options: Duck Boat Tours, Old Town Trolley Tours, Boston Harbor Cruises, Whale Watch, Fenway Park Tour, USS Constitution Tour, or Boston Movie Tours.

Autumn Special Events

Fall in New England is essentially the season of festivals, so there are lots of special events going on in and around the city. Here are some local and tourist favorites:

  • Head of the Charles Regatta: Held at the end of October, the Head of the Charles attracts 11,000 of the best crew athletes and tens of thousands of spectators to Boston to watch two days of rowing competition on the Charles. This legendary event is fun for spectators and athletes of all ages.
  • Frog Pond Pumpkin Float: This newer event is fun for the whole family; gather at Frog Pond at Boston Common to see the thousands of floating pumpkins, jack-o-lanterns, and luminaries.
  • HONK! Festival: Takes place every Columbus Day weekend and attracts some of the best bands and acts to Somerville for a three-day celebration of music.
  • Oktoberfest: Boston is home to many breweries, so it’s no surprise the city has a plethora of Octoberfest activities. Sam Adams and Harpoon both have large gatherings to celebrate, but there are also events at City Taphouse, Nightshift Brewing, and more.

Winter Boston Getaways

There’s something inviting and romantic about freshly fallen snow in the city. Experience it for yourself with a pre- or post-holiday trip to Boston.

Friday Evening

What’s the absolute best thing to warm you up on a cold winter’s night? Fresh, delicious, Italian food.

If you’ve never visited, you have to check out the North End. Boston’s version of Little Italy boasts authentic Italian meals served in an authentic atmosphere, just steps from the water and the TD Garden.

Some fan favorites in the North End – though some will argue you can’t get a bad meal there – include:

  • La Famiglia Giorgio’s: Their hearty portions and homemade pasta make this place a fan favorite. Named one of the Top 5 Italian Restaurants in Boston, if you’re looking for tried and true Italian cuisine, La Famiglia Giorgio’s is a safe bet.
  • Mamma Maria: If you’re celebrating a special occasion, after all this is the holiday season, a great choice is Mamma Maria. A little on the pricey side, but totally worth it – it is the only 4 Diamond Rated Italian restaurant in the city. Their menu is influenced by the season and changes daily, so be sure to check their website before you go.
  • Bricco: This is a popular stop for athletes and celebrities alike, and we know why. Their menu boasts a huge variety of authentic fare that incorporates the best of New England dining with classic Italian dishes.

If you’re not stuffed after your meal, the best part of dining in the North End might be grabbing dessert from Mike’s Pastry, the world-famous cannoli shop that’s been there since 1946.


Just because it’s winter time doesn’t mean you can’t partake in some outdoor activities. On a sunny day in the city, there are a few out-of-doors attractions you won’t want to miss.

Try your hand at ice skating on the Frog Pond at Boston Common. Admission is relatively inexpensive, they offer skate rentals, and you can glide around the historic park and take in the sights and sounds of downtown Boston.

If you’re really into skating, check out the skate path at Boston Winter, part of the “Boston Seasons” attraction at City Hall Plaza. While they couldn’t open in 2018-2019 due to the warm weather, this skating path should be good to go this winter, and boasts food, drink, warming shelters, and shopping to keep everyone entertained.

Sometimes the cold can just be too much, especially for the kiddos, so we recommend a couple of family-friendly, indoor activities that will surely get them in the spirit of the season.

  • Boston Children’s Museum: Throughout the months of December, January, and February, Boston’s Children’s Museum hosts a variety of activities during their Winter Wonderland celebration. There are interactive exhibits, live musical performances, arts and crafts, games, and more. Despite the name, Boston Children’s Museum truly has something fun for the whole family.
  • Legoland Discovery Center: Their annual celebration, dubbed the Holiday Bricktacular, runs on select weekends in the winter. Kids and adults can partake in building competitions, scavenger hunts, and more surrounded by a winter and holiday-themed Lego wonderland.

Saturday Evening

Saturday evening is a great time to catch a show in Boston’s renowned Theater District. Home to the Boston Opera House, Emerson Colonial, the Boch Center (formerly the Wang), the Shubert, the Wilbur, and the Orpheum, the Theater District plays host to seasonal shows and performances the whole family will enjoy.

For the 2019-2020 season, a few of the holiday-themed shows worth exploring include:

More shows will be added to the calendar as we get closer to the winter season, so be sure to check out the theaters’ websites for additional information.

No matter what you have planned for Saturday night, make sure you set aside time to see the beautiful lights and decorated trees in the city. Boston Common is home to the city’s “official” Christmas tree, donated from Nova Scotia every year since 1971. The second holiday installation you should see is at Faneuil Hall, where Blink!, the Christmas light show, runs nightly from late November to January.

After dinner, we highly recommend checking out the Igloo Bar at the Envoy Hotel. On their rooftop, Envoy has set up six heated igloos that have a spectacular view of the city skyline. Bar service attends to each igloo, so you can sip a delectable cocktail while you “chill” out in style.


Before your winter weekend getaway comes to a close, there are plenty of cozy activities to try in Boston. One of the best ways to warm up is with delicious drinks and treats, so here are a few food-themed lazy Sunday to-do’s to add to your list.

  • Snowflake Afternoon Tea at the Langham: Get the royal treatment with afternoon tea at the Langham Hotel. Served with pastries and sandwiches inspired by the season, this cozy stop is great before you head back home.
  • Bites of Boston Food Tour: These private and group tours take you through different neighborhoods in the city, where you can sample classic Boston eats such as lobster and chowder. You can also go the sweet and savory route, which takes you through the eclectic food scene in the South End.
  • Try the Hot Chocolate Flight at Met Back Bay: Arguably the best hot chocolate experience in the city, this flight of four varieties of this treat go way beyond Swiss Miss. Flavors like dulce de leche and spiced Mexican bring a whole new meaning to the term hot chocolate.

Winter Special Events

Winter is also full of special events, but these three bring a little bit of fun for everyone. Pro tip: In the weeks leading up to your trip, check out Thrillist for a list of all the cool events in Boston for the dates you’ll be there.

  • Boston Holiday Pops: This beloved Boston holiday tradition usually opens during the first week of December at the Symphony Hall. Conductor Keith Lockhart leads the Boston Pops through some of your favorite holiday tunes, and you can even participate in the sing-along. A jolly special guest usually arrives, so be sure to check the details of your tickets.
  • Boston Tea Party Re-enactment: Held every year on the anniversary of the real Boston Tea Party (December 16), this quirky tradition is usually packed. The evening begins at the Old South Meeting Hall, before everyone – audience and re-enactors alike – make their way to Griffin’s Wharf for the main event.
  • First Night Boston: This isn’t so much a singular event as it is a day and night full of celebration, activities, entertainment, and fun. The lineup changes every year, so make sure you check it out in advance. A few can’t-miss attractions include live music in Copley Place, and the light-up ice sculptures and fireworks in Boston Common.

Spring Weekends in Boston

Spring in the city is an exciting time. The cold of winter is slowly leaving, making way for the warmth of a new summer. That in between season, spring, blossoms with lots of activities and entertainment opportunities that draw Bostonians out of hibernation. If you’ve got cabin fever yourself, one of the best getaways right in your own backyard is Boston!


Depending on the weather, Friday afternoon can be a great time to take a stroll along the Esplanade. A true sign of spring in Boston is when you can see troves of locals walking and running along the Charles and the Esplanade, which gives you a great view of the city skyline and Cambridge.

Finish your walk and head to the Public Garden to see the blooming cherry blossom trees along Beacon Street in Back Bay. This whole area is beautiful in spring and definitely shouldn’t be missed.

Since you’re in the neighborhood, Back Bay also has many dining options for your first night in the city. This neighborhood is packed with local and tourist favorites, so these are just a few that we recommend:


A spring Saturday is a great time to head over to Boston Harbor, where you can enjoy a day on land and on the sea. There are a variety of options that get you out on the water:

  • Whale Watch: Boston Harbor Cruises runs whale watches year-round, running about three hours and taking you out into Massachusetts Bay to search for these majestic creatures.
  • Sightseeing Cruise: This 90-minute cruise will show you relics from the Revolutionary War, legendary haunts, and islands and lighthouses throughout the harbor. This tour is entirely narrated, and you’ll walk away with newfound knowledge about the historic Boston Harbor.
  • USS Constitution: Known as “Old Ironsides,” this was the first ship commissioned by the U.S. Navy. This 45-minute tour will show you the nearby Naval Yard, Bunker Hill Monument, the Old North Church, and the site of the Boston Tea Party.

Once you’ve come ashore, or if you never left, there’s still lots to do in this neighborhood. Faneuil Hall and Quincy Market are right there, so there’s plenty of food and drink options. Christopher Columbus Waterfront Park is a nice place to take in the salty air and recuperate before your Saturday night fun.

Saturday Evening

Most people don’t associate spring time with hockey or basketball, but this is actually one of the most exciting times in the season. The Boston Bruins and Boston Celtics are typically winding down their regular season and gearing up for the playoffs, making this night the perfect chance to go see a game. Depending on when you go, you might even be able to catch a playoff game, which is one of the most exciting events in sports.

The Bruins and the Celtics both play at TD Garden, which has recently undergone a renovation and expansion. The Hub on Causeway will be home to residences, grocery stores, restaurants, and music venues, but isn’t completely finished. Until then, the restaurants and bars surrounding The Garden are a fantastic option before puck drop or tip off. We love:

  • The Greatest Bar: Home to possibly the greatest chicken tenders known to man, the three floors of the greatest bar feature plenty of music, food, and drink to fill you up before you head directly across the street to the game.
  • The Harp: The Harp has been serving game-goers and regulars alike for almost 30 years. It has a full menu of delicious bites and over 20 taps, so everyone can find something they enjoy.
  • Sullivan’s Tap: If you’re looking for an authentic experience, look no further than Sullivan’s Tap. This cash-only establishment has been popular amongst locals for years, and is the perfect place to grab a cheap drink and play games with your friends.


If the previous day just wasn’t enough for you, a spring Sunday in Boston is a great chance to make your way out to Somerville. Assembly Row is a shopping, dining, and entertainment outdoor mall, and literally has something for everyone in your group.

You can outlet shop at their stores, which include Nike, Polo, Saks Fifth Ave, and more. The dining options are anything but ordinary, and you can find inner-city staples like Legal Seafood and Mike’s Pastry right at the Row. Lastly, if you’re looking for something to do, Assembly Row is home to Legoland Discovery Center, Muse Paintbar, and Lucky Strike Social, which has bowling, billiards, shuffleboard, and more.

Spring Special Events

The springtime special events in Boston are some of the most famous events that the city is known for. If you can make time to be in Beantown for one of these days, you won’t regret it.

  • St. Patrick’s Day: Boston is arguably one of the most Irish cities in the country, so you know they do it up right for this Irish holiday. The Annual St. Patrick’s Day Parade is held in South Boston, otherwise known as Southie, and takes place on the Sunday closest to the holiday. This day can get pretty wild, but it’s also one of the best St. Patty’s parades in the entire country.
  • Boston Marathon: The world’s largest annual marathon sees over 20,000 runners make their way from Hopkinton, Massachusetts, to downtown Boston on Patriots’ Day. Over 500,000 people watch and cheer on the runners, and the day-long event kicks off around 9 a.m. Technically this isn’t held on a weekend, but with Patriots’ Day being a holiday for Maine and Massachusetts, it might as well be.

No matter what your tastes are, you’re guaranteed to find fun things to do during a weekend in Boston. To make your life even easier, Concord Coach will handle the transportation for you! Round-trip rides to Boston run daily from many of our New Hampshire and Maine locations, so check out our website or contact us for more information.