Plan an Autumn Weekend Getaway to Boston

One of my favorite places to visit in the fall is the city of Boston. (Photo courtesy of

If you leave a comment at the bottom of this post and let me know why you love Taylor Swift, you could receive two free tickets to her San Diego or Phoenix shows THIS WEEK! Read through the post to find out how.

If you are: seeking changing leaves and cooler weather, a sports enthusiast, a history buff, or just looking for some authentic Halloween adventure, then set a course for Boston for an autumn weekend getaway.

Boston is a breathtaking mix of historic and modern architectural wonders coupled with vibrant culture, dining and shopping. According the Hotel Price Index from, Boston is the 5th most popular East Coast City amongst both American and international travelers.

Seasonal Suggestions for a fall vacation in Boston

Fall Foliage in Boston is at its peak during the last few weeks of October. You can take in the vibrant leaves all over the city. Turn your kids’ fall break into some educational fun as you stand along the waterfront where the Boston Massacre took place or take in the Bunker Hill Monument site of the famed Revolutionary War battle. Be sure to cruise (by foot or rent a bicycle) the 2 ½ mile Freedom Trail where you can take in 16 historic sites including the USS Constitution and Paul Revere’s house.

Savings on Site-Seeing

The Family-Friendly Value Pass available through the Greater Boston Convention and Visitors Bureau through the end of October makes it easy to stay and play affordably in Boston. It is a free pass, which offers substantial discounts and freebies at a variety of venues and eateries throughout the city. Another avenue of savings is the Boston City Pass, which gives you admission to five signature attractions and a significantly reduced cost.

A Brew Tour or Two

For fans of authentic New England brews, tickets are available for the Freedom Trail Pub Crawl every Tuesday at 5:30 P.M. from the ArtsBoston Booth at Faneuil Hall. Call (617) 357-8300 for more details and to make a reservation. For a suggested donation of $2 – all of which goes to support local charities – beer enthusiasts can also enjoy an affordable tour of the Sam Adams Brewery, including product samples and historical factoids about the famed brewer himself.

Haunted Happenings

Boston is one of the most haunted cities in America and with Halloween right around the corner, the tricks and treats are around the city.

Head up the coast just 16 miles north of Boston to the town of Salem, the infamous site of the 1692 witch trials, and join the town’s popular one hour outdoor candlelit tour, led by well-known historian and author Jim McAllister. The tour explores the sites and story of the witch trials, Salem’s darkest hour. Catch the tour Thursdays through Sundays through October 30th at 7pm.

Get your scare on at the The Fear at Fenway at historic Fenway Park with three ‘spooktacular’ attractions and even a lights-on version for the kiddos. Another popular attraction is the Ghosts and Gravestones Tour around Boston led by a host of ghoulish characters.

Hotels in Boston

A wonderful hotel for its location and service is the Omni Parker House Hotel.   It’s also Boston’s most haunted hotel. Plan a visit with some of the hotel’s more bizarre and permanent guests. Prices of hotel rooms in Boston are going up, HOWEVER, Americans are also spending more, both domestically and overseas –spending an average of $5 more a night on U.S. properties and $11 more at hotels internationally over last year.

Traveling during the fall is one of my favorite times to explore a new city but don’t let the season keep you from seeing Boston. And when you go: be sure to brush up on your New England speak. If you want to sound like a local in Boston, take some tips from The Wicked Good Guide to Boston English.

I can’t believe we’re already halfway through October and nearing November! November’s ‘City of the Month’ post will highlight the wonderful city of Phoenix, Arizona. In honor of November’s ‘City of the Month’ we are giving away two sets of Taylor Swift tickets for her San Diego (Thursday, October 20) and Phoenix (Friday, October 21) shows. If you’ll be in either of these cities THIS WEEK, leave a comment telling us why you love Taylor Swift and what city you would like to see the concert in for a chance to receive two free tickets. Good luck!



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21 Responses to “Plan an Autumn Weekend Getaway to Boston”

  1. Beverly says:

    I like Taylor Swift because she is a good role model for young people. My daughter and son love her music. We live in Phoenix and would totally love to see her live!

  2. evic says:

    My daughter loves Taylor Swift and I love my daughter!!! It would make her year to see one of her favorite artist live and it would make mine to give her this type of opportunity otherwise not attainable right now because of a tight budget:( So I hope that I get lucky here to bring her to the San Diego show on the 20th. Thank you for the contest!!!

  3. Tiphanie Pearson says:

    The reason I would want the Taylor Swift tickets, is because me an mom listen to Taylor everyday. We have every album. She is my inspiration. We have never been to one of her concert’s. Please it’ll be great for me and my mom.

  4. steven says:

    I would love to see Taylor Swift in San Diego she is amazing, beautiful, talented, and seems like a really good role model. Taylor is my favorite singer :)

  5. Laura Prakel-George says:

    I love Taylor Swift because moms can be comfortable having their daughters look up to her and not worry about what kind of role model she is.

  6. Daniel High says:

    I’d love the tickets to the Phoenix concert. I think Taylor is the perfect combination of country and pop. In the age of the vanishing singer/songwriter Taylor stands tall.

  7. Jennifer Kelly says:

    I love her because she is perfect for not only my six year old who adores her and knows every song, but also for my 14 year old. Taylor Swift has worked hard, stuck to what she believes and is not afraid to say what she thinks. I would love to take my girls to the concert!

  8. Kayleigh says:

    Taylor Swift is an incredible performer/entertainer. It is wonderful to see someone in the business be such a power role model for girls of all ages. Her guinely kind spirt also never ceases to amaze me.

    My newphew also claims to be one of Taylor’s (or tswizzle as he likes to call her) biggest fans and I would love to be able to take him to a concert in San Diego.

  9. Rachelle K. says:

    Besides her stellar voice and music – I love that Taylor Swift is a great role model for younger women. I would love to take my high-school aged niece to the San Diego show. This would be her first official concert and the perfect one to attend!

  10. My wife and daughter of 4 years old, both break out in song together whenever a Taylor Swift song comes on, and it would be their dream to see her here in Phoenix! They tried for days to win them on the radio with no luck getting through, and they would be so surprised to win them! A concert with Taylor would be a lasting memory for them both!

  11. Laura Prakel-George says:

    Re: Comment No. 5 –

    And just in case, we live in Phoenix and would love to see Taylor live in concert.

  12. Eileen H. says:

    I love Taylor Swift because I can relate so well to her music. She sings about life experiences that pull at my emotions, because I went through the same events when I was younger. I’d love to win the Phoenix tickets.

  13. Anne Badasci says:

    Ever since I heard Tim McGraw on the radio for the first time, Taylor’s music and the poise and grace she exhibits every single day have inspired me and changed me for the better. I have every magazine cover she’s ever been on, posters everywhere, and she is the reason I saved up, bought a guitar, and play for hours every week! I could not imagine anyone being a bigger fan, I would give anything I own to meet Taylor and just tell her what her music and her inspiration have done for me. And of course, ask her how she gets her hair to be so curly! I love Taylor so, so much and would be SO excited to attend her show in beautiful San Diego or Phoenix!

  14. Jessica Killackey says:

    I would love to see Taylor Swift in San Diego because she is not only a wonderful singer, but she is a wonderful person. She has shown time and time again that she won’t bend to match the status quo, or what’s hot. She is her own person, and isn’t afraid to show it. When rudely interrupted by Kanye West, she stayed calm and kept it together; this shows that Taylor can take whatever her critics say and not take it completely to heart, put it aside, and continue strong. The fact that all of her music is written by her really inspires me because she can take things as scary as a first day of school, bullying, a depressing break-up, secret crushes, and admitting a crush on someone and make it relevant to all ages, no matter they are 6 or 666. She is also inspiring because she can take even the scariest and saddest things and make them into hit songs that everyone can sing along to. Another amazement for me is her age; she is a true musical genius and she is only the awe-inspiring age of 21 years old. Taylor Swift is my idol, and being able to see her show would be my life’s fulfillment.

  15. Justin Taylor says:

    My parent’s bought me Taylor Swift’s album, “Fearless”, for Christmas back in 2008. They had also, as part of a longstanding tradition, purchased me a $25 Starbucks gift card.

    Christmas morning I took the new CD and my gift card out to my car, which I had only had for a few months, and stuck the cd into the player.

    Starting my car, I pull out of the driveway and start to head to Starbucks. Windows down, sunroof open. The weather was perfect. It had rained the night before – an Arizonan’s “White Christmas”.

    It felt like a scene out of the movies, as Taylor’s voice came on track one, Fearless.

    “There’s something ’bout the way the street looks when it’s just rained; there’s a glow off the pavement…”

    And I believe I will give a nod to The Perks of Being a Wallflower – because at the moment, I swore I was infinite.

    If I won these tickets, I would love to see her in Phoenix.

  16. Megan says:

    The reason why I love Taylor Swift so much is she is just such a great entertainer and I can relate to most if not all her songs. My friends laught at me when her songs come on the radio and I blast it and sing along. I have been trying for weeks to win some tickets to the Phoenix show and it would be my dream to go!

  17. Anonymous says:

    When will you announce the winner? Good chance the winner will need to make arrangements such as sitter. Thank you!

  18. Sherry says:

    My nephew, who lives in Phoenix, is a major Taylor Swift fan! He turned me on to her music and now I’m a major Taylor fan (even 47 year old ‘girls’ love Taylor)!
    I would so love to win these tickets for him so I could return the favor. He’s one of the good guys! (I love you Justin Taylor!)

  19. Dawn C says:

    I would love the tickets for the Taylor concert in Phoenix. It would be a great belated birthday present for my brother. I kinda owe him because I got married the week of his birthday. :)

  20. Nicole says:

    Thanks for your interest, winners have been notified. Please look back for future Travel Smart Blog contests!

  21. Anonymous says:

    I’m sure everyone is curious…who won?

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