Ah fall, the dreamy season of warm earthy colors, cozy sweaters and beautiful weekends. As much as most of us LOVE summer, there is something so magical about fall, especially in the Northeast region of the United States. It is the perfect time to have a fabulous fall New England weekend getaway!
If you are looking to experience all of the wonders that fall offers, then booking a getaway to New England will leave you and your loved ones speechless. Between charming Colonial downtown areas, to forests full of foliage and quaint wineries, to cozy restaurants, there is so much to enjoy during a fall weekend trip to New England. But exactly where should you go?
I am Taylor Deer, a world traveler who has visited 4 continents and most of the US, and the owner of the travel site Brown Eyed Flower Child. (You may already know me from my previous article, Southern California Weekend Getaways.) In my northeast US travels I have found four favorite weekend destinations in New England that I think you will love: Portland, Maine; Boston, Massachusetts; Newport, Rhode Island; and Mystic, Connecticut.
Four Fabulous Fall Weekend Getaways in New England
There are a ton of options for fall weekend trips in New England, or any time of year weekends. I won’t say these are the best, but I will say these 4 are my favorites. You may love all 4 of these great cities so much that you may want to make a full vacation out of your visit. Or you could make a fabulous New England coast road trip visiting all 4 of them. If you do this though, consider starting a bit farther north, at Acadia National Park, and maybe even continuing on down to New York City to end your trip with a bang! But if you are just looking for a New England weekend getaway, take your pick!
Fall New England Weekend Getaway #1 – Portland, Maine
One of the most underrated cities in America is Portland, Maine. This beautiful fisherman city is filled with so many quaint neighborhoods, restaurants, shops and adventure. It is the perfect city to travel to during the fall season. Hopefully our introduction intrigues you, so you may want to know more about the best things to do in Portland, and start planning a trip!
Seafood in Portland:
You cannot travel to Portland, without indulging in some amazing seafood! Situated near the city’s popular wharf are some of the best restaurants for fresh local catches, shellfish and chowders. A few places you cannot miss when you go to Portland are Boone’s Fish House & Oyster Room, Gilbert’s Chowder House and DiMillo’s Restaurant and Lounge.
Nightlife in Portland:
In addition to Portland’s dining scene, the city also offers a wonderful nightlife for all to enjoy. If you are looking for a classy cocktail bar to lounge at, Vena’s Fizz House is the perfect place! This corner-side cocktail house features a charming, turn-of-the-century atmosphere with a plethora of drink options that are both alcoholic and non-alcoholic.
For those who prefer a classy Irish pub, then Bull Feeney’s is the place for you! This two-story tavern hosts some of Maine’s best cover bands. It also offers a plethora of great drinks, especially beer! If you are looking for a place where you know you will have a good time, then Bull Feeney’s is where it is!
On the other hand, there is a great place for those who are looking for cheap beers and to just have a good time! 3 Dollar Dewey’s is where you could get drinks for only a couple dollars while having fun! This great local bar is a wonderful place to play some games and make new friends. It is perfect for the 20-something or college student.
Nature in Portland:
Besides eating and drinking, Portland also offers some amazing nature. The Eastern Promenade is a breathtaking coastal trail that was built along an old rail corridor that offers beautiful views of the harbor and Casco Bay. On a nice day, you will spot plenty of sailboats in the water, people hanging out on the lawn and East End Beach as well as little puppies playing in the chilly bay. Besides walking around this 2.1-mile trail, there is also a train around the promenade that you can take and learn more about Portland.
Lighthouses in Portland:
You cannot leave Portland without seeing some of the city’s famous lighthouses. When you make your way over to South Portland, you could see the Spring Point Ledge Light. This tower is built out of brick instead of cast-iron (unlike the others in the area) and is situated at the end of a 900-foot breakwater. The large pieces of rock allow you to easily walk across the breakwater to the lighthouse.
Located a little outside of the city in Cape Elizabeth is the stunning Fort Williams Park where you could savor fall foliage along the beautiful cliffs of the Casco Bay. It is at this park where you could spot the famous Portland Head Light. It is absolutely beautiful and a perfect spot to be during autumn’s prime!
Fall New England Weekend Getaway #2 – Boston, Massachusetts
Boston is definitely a city you cannot miss out on during the fall season. There are so many charming neighborhoods in this city that you will fall in love with, especially during autumn. If our overview interests you, and you are planning a trip, check out this detailed plan for 48 hours in Boston.
One of the best areas in the city is Beacon Hill. Known as one of the most desirable and expensive neighborhoods in Boston, you could find high-end restaurants, cute coffee shops, flower stores and adorable boutiques in this section.
Another place to wander through on a beautiful day in autumn is the Boston Public Garden. This lovely park has different walking paths, beautiful Spanish moss trees, adorable animals and a lovely bridge that goes over a small pond.
Food in Boston:
Boston is also known for its amazing food! They have wonderful brunch spots, Irish pubs, lobster roll cafés and Italian restaurants. One of the best places to grab brunch is at Clink (located in The Liberty Hotel). This posh brunch and dinner spot used to be the old Charles Street Jail that held some of Boston’s most notorious criminals. It is definitely a place you want to check out and the brunch is amazing!
In addition, the Liberty Bar in the hotel also has amazing lunch and dinner meals. It is a great place to hangout at night as well! The wine is definitely on point.
If you are looking for an amazing lobster roll place, Pauli’s is the place to go! You could get either a Connecticut lobster roll that is heated with brown butter or a Maine lobster roll that is served cold with mayo. Either one is an amazing option!
In addition, you cannot make your way to Boston without a great Italian dinner. One of the best Italian restaurants in Boston’s Faneuil Hall district (also known as Boston’s Little Italy) is Dolce Vita Ristorante. Everything is tasty and delicious, plus the owner will come around to all tables and introduce himself!
Bars in Boston:
Not only is Boston known for its food, the bars are also amazing! Since Boston has a large Irish American population, there are plenty of wonderful bars and pubs to grab a fresh brew. One of the first places to stop at is the famous Cheers Bar from the famous Nick at Nite sitcom, Cheers! This iconic bar is located right outside of Boston’s Public Garden and is actually much bigger than what you could imagine. There are three rooms: the original bar where they shot the show, a restaurant area and another bar that overlooks the park. It is a place that everyone will enjoy!
Two other popular spots to enjoy some beer and even the beautiful fall weather are at Samuel Adams Brewery and Harpoon Brewery.
Fall New England Weekend Getaway #3 – Newport, Rhode Island
A wonderful and relaxing fall getaway is in Newport, RI. This beautiful city is home to some exquisite mansions, scenic vineyards, fine dining, beautiful nature and so much more.
Newport’s Mansions:
One of the top things to do during your time in Newport is tour the lavish mansions. The most impressive mansions that visitors MUST visit during their time in Newport are The Breakers, The Elms and Marble House. The Breakers was the summer home to Cornelius Vanderbilt II. The Elms, on the other hand, is famous for being modeled after the French Château d’Asnières. Lastly, the Marble House has over 500,000 cubic feet of marble. You will be amazed as you tour these stunning estates!
Newport’s Vineyards:
In addition to touring the mansions, it is highly recommended to also check out Newport’s vineyards. The wineries in and around Newport are some of the most renowned in New England and it also gives you the opportunity to savor fall foliage as most of them offer seating and tastings outside. Some of the best wineries in and around Newport are Newport Vineyards, Carolyn’s Sakonnet Vineyards and Greenvale Vineyards. During your time at Newport Vineyards, you could enjoy live music on the outdoor patio and taste amazing wines by the fire.
Carolyn Rafelian, the founder of Alex & Ani jewelry, owns Carolyn’s Sakonnet Vineyards. At this wonderful winery, there is an outdoor café, multiple tasting rooms and a big lawn to enjoy a bottle of wine with some cheese and cured meats. There is nothing better, especially on a colorful autumn day.
Lastly, Greenvale Vineyards are located along the Sakonnet River. It is a beautiful place to taste delicious wines, enjoy one of the winery’s special events and even learn some history. To top it off, they even have local food trucks! What could be better?
Dining in Newport:
In addition to wine tasting, you cannot miss out on some of Newport’s amazing restaurants. Between seafood, Italian, Irish and many other cuisines, you cannot go wrong by eating out in Newport. Here are some amazing restaurants to dine at during your time in this charming city: Benjamin’s Restaurant and Raw Bar (seafood), Pasta Beach (Italian), Diego’s (Mexican), Smokehouse (BBQ), Brick Alley Pub (Irish Pub), The Red Parrot (American), Scales and Shells (seafood), The Black Pearl (seafood), The Newport Lobster Shack (specifically lobster) and many more.
Nature in Newport:
One of the best ways to fully embrace fall in Newport is by enjoying the nature! Throughout the city are a few beaches, parks and nature trails. Newport’s First, Second and Third Beaches offer something for everyone, including the famous Cliff Walk along the water; an aquarium; a carousel and wildlife refuge. These wonderful nature spots are also great areas to get a workout in. There is no better way to enjoy the fall than in these enchanting nature spots!
Fall New England Weekend Getaway #4 – Mystic, Connecticut
Mystic is a small, but thriving city on the Connecticut coast. The historic downtown features charming New England architecture along with great restaurants, boutiques and gift shops, and the surrounding area has a plethora of cideries, vineyards and breweries, as well as areas for outdoor exploration. If you are considering a visit, you may want to know more about the historic Whaler’s Inn, one of the finest places to stay in Mystic.
Food in Mystic:
Some wonderful things to eat while you are downtown are a Connecticut lobster roll from Chapter One or a slice of pizza from the famous Mystic Pizza!
Connecticut lobster rolls consist of chunks of lobster meat with melted brown butter and fresh herbs on top. It is usually served in a toasted brioche bun and is absolutely delicious. Chapter One is a great place to grab a traditional Connecticut roll in downtown Mystic. They also have a great brunch on the weekends!
In addition to lobster, Mystic Pizza is another hotspot in this city where the famous 1988 Julia Roberts’ film “Mystic Pizza” took place. Not only could you savor a “Slice of Heaven” at Mystic Pizza, but it is also a wonderful place to grab a beer, relax and feel like Julia Roberts. There are photographs, from the film, hung throughout the restaurant. It is a cool spot!
Things to do in Mystic:
Besides downtown, there is so much more that Mystic offers. Another area to pay a visit to is Olde Mistick Village. This popular place has a Colonial New England vibe with amazing shops, restaurants, entertainment and so much more! Located right next to Olde Mistick Village is the famous Mystic Aquarium that features sharks, stingrays, jellyfish, sea lions and more. The aquarium is a place where everyone will be amazed!
Nature in Mystic:
In addition to historic downtown and Olde Mistick Village, the Mystic area also offers numerous fairs and festivals, state parks, beaches, local farms, wineries, breweries and cideries to fulfill your fall desires.
Esker Point is a scenic beach area in the neighboring town of Noank. In addition to spending time at the beach, you could admire some beautiful Victorian houses. It is such a beautiful and quaint area!
Another gorgeous place to visit in the Mystic area is Bluff Point State Park in the town of Groton. This beautiful park is a peninsula that offers over 800 acres of hiking and bike trails, fishing facilities, wildlife and so much more. It is also a wonderful place to watch the sunset along the Long Island Sound.
Ready to plan your fall New England weekend getaway??
I hope you all enjoyed this guide for fall New England weekend getaways. We can’t say that these are the absolute best weekend getaways in New England in fall. In fact we had to throw in another option, at Bar Harbor, Maine. We can say with surety, they are all amazing. These cities keep you right along the Atlantic for beautiful ocean sunrises and amazing seafood, along with those brilliant fall colors!
And if your aren’t heading to New England anytime soon, we have weekend getaways all over the US.
Can’t make it this year? Pin it for next!
About Taylor Deer
Taylor is a world travel blogger, writer and content creator from New Jersey who created Brown Eyed Flower Child to show the world through her eyes. The travel bug bit Taylor when she studied abroad in Salamanca, Spain during summer 2012. Ever since then, Taylor’s sense of wander has expanded to several different countries and regions in Europe, Asia and Africa as well as throughout the United States. Whether she is traveling to get out of her comfort zone and find herself, to gain better insight on the world, to help someone or participate in an event or retreat, each travel journey is special and means something different to her. For more travel articles and inspiration, visit Taylor’s blog at www.browneyedflowerchild.com or follow her on her Facebook page, or Instagram.
