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School is officially back in session but that doesn’t make for a lack of fun things to do all throughout the month of September!

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When most people think about the month of September their mind immediately goes to back-to-school and the mark of the end of summer. Sure, September marks the end of the summer season but that doesn’t mean it is devoid of just as many fun and festive happenings. Labor Day Weekend kicks off September on a high note, sneaking in one last holiday weekend before school starts up again, and things just keep going up from there.

September also begins the fall extravaganza that takes over Long Island every year around this time. As the leaves begin to change color and the weather starts to cool down the farm stands open up their doors for apple picking and hayrides. It’s the perfect time to go out for a long hike, be out in nature, and view the changing of the seasons in person.

Be sure to check out our 2014 Labor Day Weekend Guide for events happening exclusively over the holiday weekend.

Fairs, Festivals, & Events
With the festive month of Fall rolling in, a myriad of festivals, fairs, and events will be going on all across the Island.

Seaford Summer Festival FREE
Seaford Long Island Railroad Station, Sunrise Highway, Seaford, NY 11783
Monday, September 1st, 11 AM - 6 PM

Stop by the Seaford Summer Festival and check out all of the unique gifts, arts & crafts, antiques, and new merchandise.

East Northport Annual Festival FREE
Main Street, East Northport, NY 11731
Friday, September 5th - Sunday, September 7th

Take the family out for a fun-filled day of tasty foods, craft vendors, games, exhibits, shows, activities for all ages, and live entertainment.

2nd Annual Long Beach Super Boardwalk and Street Fair FREE
125 East Broadway, Boardwalk, Long Beach Road, Shore Road & Riverside Drive, Long Beach, NY 11561
Saturday, September 6th - Sunday, September 7th, 10 AM - 6 PM

Enjoy walking around the boardwalk and surrounding streets as you browse the craft fair and grab a bite to eat. For a fee you can even take a dip in the ocean.

3rd Annual Fiddle and Folk Music Festival FREE
Benners Farm, 56 Gnarled Hollow Rd, East Setauket, NY 11733
Sunday, September 7th, 11 AM - 7 PM

This good ol’ fashioned folk festival will have 3 stages featuring great musical groups. There will be plenty of sing alongs, a kids corner, cute animals, the big swing, and much more.

24th Annual Nesconset Day Craft & Street Fair FREE
Smithtown Blvd, Nesconset, NY 11767
Sunday, September 7th, 10 AM - 5 PM

Walk along Smithtown Boulevard to visit all of the street vendors and see all of the fun crafts and gifts for sale. Live entertainment will be playing at the gazebo all day!

Village Cup Regatta FREE
Port Jefferson Village Center, Main Street, Port Jefferson, NY 11777
Sunday, September 7th, 1 PM - 7 PM

Come out to watch 26 sailing boats race in the Port Jefferson Harbor and Long Island Sound to raise money for Pancreatic Cancer. Don’t miss out on this great event for a great cause!

St. James Day FREE
Lake Ave. from Woodlawn to Railroad Ave., St. James, NY 11780
Sunday, September 28th, 11 AM - 5 PM

Wares, crafts, food and fun for everyone will be had at St. James Day, rain or shine!

Copiague’s 7th Annual LI Family Festival FREE
Tanner Park, 90 Tanner Park, Copiague, NY 11726
Friday, September 12th - Sunday, September 14th

The festival will feature a carnival, Pet Expo, dog themed events, and much more entertainment. A great fun-filled way to spend some time with your family.

Locust Valley Street Festival FREE
Birch Hill Road, Locust Valley, NY 11560
Saturday, September 13th, 10 AM - 4 PM

Walk around this quaint little town with it’s cute shops & boutiques and up and down the streets of artisans featuring works made from wood, leather, fiber, pottery, and glass. There will be jewelry and photography featured at the street festival.

Port Jefferson Dragon Race Festival FREE
Port Jefferson Village Center, 101 East Broadway, Port Jefferson, NY 11777
Saturday, September 20th, 9 AM - 7 PM

Local and regional teams will come together to race head to head in a series of heats at the first inaugural Dragon Boat Race festival in Port Jefferson. Bring a lawn chair or a blanket and survey the race and cheer on the participants. Music and food vendors will be around to keep the event lively.

Family Festival by the Sea FREE
Lido Beach Town Park, 630 Lido Blvd, Lido Beach, NY 11561
Saturday, September 27th - Sunday, September 28th, 11 AM - 6:30 PM

You’ll have a smashing time listening to live music, jumping on giant inflatables, eating yummy food, petting animals, making sand sculptures, and taking a pony ride at this family festival. There will also be a clam-eating and rib-eating contest.

Cow Harbor Day FREE
Northport Village Park, Main Street, Northport, NY 11731
Sunday, September 21st, 12 PM - 5 PM

The morning of Cow Harbor Day will start out with a 10K race and 2K fun run/walk. After the races there will be a concert by a Jimmy Buffet tribute band, decorated boats lining the docks, a parade, and sidewalk sales and vendors.

Hispanic American Heritage Street Fair FREE
La Fuerza Unida Inc. between Bridge Street and Glen Street, Glen Cove, NY 11542
Sunday, September 28th, 11 Am - 5 PM

Everyone, no matter their ethnicity, can come out and enjoy the Hispanic American Street Fair. The fair will feature lots of dancing, food, live music, games, and prizes.

Greek Festival on the Harbor FREE
North Hempstead Beach Park, West Shore Road, Port Washington, NY 11050
Friday, September 26th - Sunday, September 28th

Live music, food, games, rides, a flea market, and fireworks on Saturday night await all those who plan on going to the Greek Festival. Be sure to try the many Greek dishes, like, souvlaki, gyros, baklava, and loukoumades.

5th Annual Over 50 Fair
Melville Marriott, 1350 Walt Whitman Road, Melville, NY 11747
Sunday, September 28th, 10 AM - 4:30 PM
$6 - $8, free for Veterans

This annual over 50 fair will include over 90 different exhibitors, and 30 intriguing classes about health & wellness, home improvements, financial planning, travel, restaurants, and more. There will also be free valet parking and health screenings.

Seafood Festival at Sunken Meadow Park
Sunken Meadow State Parkway, Kings Park, NY 11754
Wednesday, September 3rd, 6 PM - 9 PM

Bring the whole family out for a night of live music, food, entertainment, and free giveaways for kids. For $26 you can get ½ a lobster, steamed clams and mussels, corn, shrimp, and potatoes.

Maritime Festival 2014
East End Seaport Museum, 3rd Street & Wiggins Street, Greenport, NY 11944
Friday, September 19th - Sunday, September 21st

This 3-day festival is a fundraising weekend to support the restoration of the Long Beach Bar “BUG” Lighthouse and other educational projects. There will be food, music, vendors, art, family fun, and a parade to celebrate.

Bayard Cutting Arboretum Annual Fall Garden and Harvest Festival 2014
Bayard Cutting Arboretum, 440 Montauk Highway, Great River, NY 11739
Sunday, September 28th
$15 per vehicle

This event will feature horticultural and landscape displays, educational exhibits and demonstrations, kid friendly activities, food, live music, a model train display, local artisan vendors, pumpkin painting and hay rides.

Craft & Fine Arts Fair
Nassau County Museum of Art, 1 Museum Drive, Roslyn Harbor, NY 11576
Saturday, September 27th - Sunday, September 28th, 11 AM - 6 PM
$8, children 12 and under are free

Held outside on the museum grounds, this craft fair features blown and stained glass, jewelry, pottery, furniture, wearable art, and more. Craft demonstrations will also be going on around the fairgrounds.

Breast Cancer Victory Day Family Festival
Mather Hospital, 75 N. Country Road, Port Jefferson, NY 11777
Saturday, September 27th, 12 PM

Show your support by coming out to Mather Hospital for a health fair with interactive exhibits, a breast cancer survivor inspirational speaker, zumba lessons, a giant operation game, entertainment from the main stage, and a family fun zone with plenty of things for kids to do.

Wildwood Fall Festival
Wildwood State park, Hulse Landing Road, Wading River, NY 11792
Saturday, September 27th, 11 AM - 4 PM
$8 parking

Wagon rides, pony rides, funny photos, inflatables, vendors, and much more, will be at the Wildwood Fall Festival. Don’t forget to save up your appetite for the pie-eating contest!

Kite Festival
Long Island Maritime Museum, 88 West Sayville, West Sayville, NY 11796
Sunday, September 21st, 11 AM - 5 PM
$2, children age 5 and under are free

Come out to the Kite Festival to make your own kites, fly them, and enjoy tasty treats while you do so.

42nd Annual Irish Festival
Hofstra University Campus, 1000 Hempstead Turnpike, Hempstead, NY 10549
Sunday, September 21st, 9 AM - 6 PM
$10, children 15 and under accompanied by an adult are free

This cultural festival will include bagpiping, Irish dancers, Irish music, Irish language and baking exhibits, and an art & drawing contest. There will also be vendors selling Irish jewelry and clothing.

Miller Place - Mount Sinai Historical Society 34th Annual Country Fair
75 North Country Road, Miller Place, NY 11764
Saturday, September 27th - Sunday, September 26th, 10 AM - 4 PM
$5, members and children under age 5 are free

Step back in time at this Civil War encampment with period gun displays, open hearth cooking, pottery making, textile talk, blacksmithing, and wampum bread making. There will also be tours of the William Miller House.

Open Days Program Garden Tour: Wainscott
Biercuk & Luckey Garden, 18 Sayres Path, Wainscott, NY 11975
Saturday, September 6th, 10 AM - 2 PM
$5 per garden & children under 12 are free

This private garden in Wainscott is opening up to the public for self-guided tours to benefit the Garden Conservancy. The garden includes azaleas, pieris, perennials, rhododendrons and a pool designed as a pond with a waterfall surrounded by beautiful plants.

Shinnecock Powwow
West Gate Road off Montauk Highway, Shinnecock Reservation, Southampton, NY 11968
Monday, September 1st, 10 AM - 5 PM
$15 admission - ages 6-12 and seniors $10 - free under age 5

Learn about the Shinnecock tribe and immerse yourself in their culture as you enjoy tribal dances, crafts, ceremonies, storytelling, demonstrations, native foods, drum & dance competitions, and fire lighting at sunset.

Pickle Festival
John Gardiner Farm, 900 Park Ave., Greenlawn, NY 11740
Saturday, September 20th, 10 AM - 4 PM
$5, children under 12 are free

The Greenlawn-Centerport Historical Association’s festival features diverse pickles, speciality pickles, jellies, jams, baked goods, farm-grown vegetables, lollipop farm train, a corn maze, hay rides, and family activities. The fun will go on rain or shine!

Grateful Fest 3
The Vanderbilt Museum, 180 Little Neck Rd, Centerport, NY 11721
Sunday, September 7th, 12 PM - 6:30 PM
$10 - $20

Enjoy a day full of Grateful Dead music, live painting, and exhibits by 50 artists. Half Step, The Electrix, Reckoning, and Unbroken Chain will also be performing.

Long Island Garlic Festival
Garden of Eve Organic Farm & Market, 4558 Sound Avenue, Riverhead, NY 11901
Saturday September 20th - Sunday, September 21st, 10 AM - 5 PM
$3, children under 6 are free

Come out to Riverhead to taste and enjoy a wide variety of garlic-inspired foods and dishes. There will also be live music, crafts,a garlic eating contest, and an iron chef garlic competition!

Antique Historical Arms Show
Freeport Recreation Center, 130 East Merrick Road, Freeport, NY 11520
Saturday, September 20th - Sunday, September 21st, 9 AM
$6, children under age 11 are free

Hosted by the Long Island Antique Historical Arms Society, Inc. this show will feature Revolutionary War and Civil War collectibles, swords, muskets, military rifles, bayonets, and sporting guns. Perfect for any history buffs out there.

Great Bridal Extravaganza
Islandia Marriott, 3635 Express Drive North, Islandia, NY 11749
Thursday, September 18th, 6:30 PM - 9 PM

Newly engaged couples and brides-to-be won’t want to miss out on this bridal extravaganza! This expo will include the latest bridal fashions, live performances, and complimentary hors d'oeuvres and dessert. One raffle prize will be a 8 day 7 night vacation!

Historic Pub Crawl
Huntington Historical Society Museums, 209 Main Street, Huntington, NY 11743
Thursday, September 18th, 6:30 PM

Join in on the fun by taking a historic walking tour of Huntington Village. Stops include 3 different pubs and the tour will begin at the Soldiers and Sailors Memorial building.

Tobay Boat Show
Tobay Beach, Ocean Parkway, Massapequa, NY 11758
Thursday, September 25th - Sunday, September 28th
$10, seniors are $8, and children 12 and under are free

Make your way to Massapequa to view the boats on display, join in on the Manhattan clam chowder contest, and listen in at the storytelling tent.

Live Music
There’s no better way to enjoy the beginning of the Fall season than by listening to your favorite bands and musical performances, live!

American Music Fest FREE
Port Jefferson Village Center, Main Street, Port Jefferson, NY 11777
Friday, September 26th - Sunday, September 28th

Over 35 performers will be playing on 4 stages at the American Music Fest. A variety of genres like, rock, blues, jazz, folk, funk, and country will all be played.

Sweet Sounds of Summer Concert Series: Wonderous Stories FREE
Smith Haven Mall, 313 Smith Haven Mall, Lake Grove, NY 11755
Thursday, September 4th, 6 PM

Taking place in the Lifestyle Village section of the mall, Wonderous Stories plays albums in their entirety for listeners to enjoy. Some crowd favorites they like to play are Abbey Road and Dark Side of the Moon. You are encouraged to bring your own chairs since seating is limited to benches and planters in the Lifestyle Village. Food sampling will also be available from some of the mall eateries and restaurants.

CopyCat FREE
JC Cove Waterfront Restaurant & Bar, 229 Woodcleft Ave, Freeport, NY 11520
Saturday, September 6th, 7 PM - 11 PM

CopyCat is one of Long Island’s top Caribbean party bands. They specialize in reggae, 80’s dance music, pop, calypso, R&B, disco, and 50’s and 60’s music. Get your groove on down at JC Waterfront Restaurant & Bar.

Eddie Money FREE
Harry Chapin Lakeside Theatre
Eisenhower Park, Merrick Ave. & Hempstead Turnpike, East Meadow, NY 11554
Saturday, September 27th, 3:30 PM

Eddie Money, American rock guitarist, saxophonist, and singer-songwriter, will have you “Shakin” as he plays a free show for fans at Eisenhower Park.

The Rising: Bruce Springsteen Tribute
The Paramount, 370 New York Avenue, Huntington, NY 11743
Thursday, September 4th, 8 PM
$15 - $25

Come out and listen to this brotherhood of friends tribute band as they play all of Bruce Springsteen’s best hits and Born in the U.S.A in it’s entirety!

Social Distortion with Special Guests The Whigs & Jonny Two Bags
The Paramount, 370 New York Avenue, Huntington, NY 11743
Friday, September 5th, 8 PM
$35 - $75

This powerful band is made up of frontman Mike Ness, longtime guitarist Jonny Wickersham, bassist Brent Harding and drummer David Hidalgo Jr. Come out to hear their perfect blend of punk-rock, bluesy rock n’ roll, and outlaw country sound.

Dead On Live
Suffolk Theater, 118 E. Main Street, Riverhead, NY 11901
Friday, September 5th, 8 PM

Dead On Live is a Grateful Dead tribute band made up of members also from The Zen Tricksters and The Shania Twain Band. Their masterful note-for-note recreation of ‘American Beauty’ and ‘Working Man’s Dead’ are not to be missed.

Live and Let Die: A Paul McCartney Tribute
Madison Theatre at Molloy College, 1000 Hempstead Ave, Rockville Centre, NY 11571
Thursday, September 11th - Friday, September 12th, 8 PM - 10:15 PM
$45 - $55

This symphonic tribute to both Paul McCartney and The Beatles stars Tony Kishman from the Broadway show Beatlemania. Some of the songs featured in the set included ‘Hey Jude,’ ‘Penny Lane,’ ‘Live and Let Die,’ and ‘Yesterday.’ Musicians from the Children’s Orchestra Society will also be in the musical act.

Steely Dan
The Paramount, 370 New York Avenue, Huntington, NY 11743
Saturday, September 13th - Sunday, September 14th, 8 PM
$75 - $250

This American jazz/rock band will be bringing their ‘Jamalot Ever After Tour’ across the U.S., making a stop at The Paramount. Come out and listen to their unique sound stylings.

Enrique Iglesias
Nassau Coliseum, 1255 Hempstead Turnpike, Uniondale, NY 11553
Sunday, September 14th, 7:30 PM
$46 - $176

Listen to the passionate vocal stylings of Enrique Iglesias in concert as he makes the audience swoon to the sound of his music, and sing along with his lyrics.

Cher D2K Tour
Nassau Coliseum, 1255 Hempstead Turnpike, Uniondale, NY 11553
Monday, September 22nd, 7:30 PM
$36 - $155

Come out to listen to this multi-talented diva, with her well-known contralto singing voice, take the stage at Nassau Coliseum.

The Space at Westbury, 250 Post Avenue, Westbury, NY 11590
Friday, September 26th, 8 PM
$35 - $55

This popular 1990s American rock, jam, progressive, psychedelic band from New York will be gracing the stage at The Space at Westbury this September!

Car & Motorcycle Shows
Put some pep in your engine at a Long Island car or motorcycle show! You’ll have a blast looking at all of the cool classic cars and motorcycles on display.

Classic Car Show FREE
Sagamore Hill National Historic Site, 20 Sagamore Hill Rd, Cove Neck, NY 11771
Sunday, September 7th, 9 AM - 3 PM

This classic car show sponsored by Long Island Sound Classic Car Club will feature all cars and trucks prior to 1949. The event is free for spectators and the rain date is September 14th.

New York AutoFest Midsummer Nights Dream Cruise FREE
Ransom Beach, 12 Bayville Ave, Bayville, NY 11709
September 5th, 12th, 19th, & 26th, 5:30 PM - 9:00 PM

Come down to see all of the cool cars cruise night. Admission for spectators is free and $5 to end a show vehicle. Weekly awards are presented to the Best in Cruise vehicle.

Wednesday Night Cruise In Garden City Park FREE
2341 Jericho Turnpike, Garden City Park, NY 11040
Every Wednesday in September, 6:30 PM - 10 PM

This weekly car cruise meets up in the King Kullen shopping center near Citibank every Wednesday night. Come out to see all of the cool cars that show up for the meet.

Oyster Bay Tuesday Cruise Nights FREE
South Street & Audrey Ave., Oyster Bay, NY 11771
Tuesday, September 2nd, 5 PM - 10 PM

Audrey Avenue will be closed down to provide ample space for all of the finest cars and motorcycles gathering in Oyster Bay. Spectators are free while show car entries cost $5. The downtown restaurants and shops will be open, so after the show grab a bite to eat and walk around.

Wednesday Night Car Cruise in Ronkonkoma FREE
299 Hawkins Ave., Ronkonkoma, NY 11799
Every Wednesday in September

Located one mile north of exit 60 on the LIE/Hawkins Avenue, this car cruise in will include antique and classic cars and provide lots of free, family fun. You can bring your own car to show off or just stop by.

Big Rig Truck Show and Fall Festival
100 Arrivals, (Use Federal Trade Zone Entrance) Ronkonkoma, NY 11779
Sunday, September 28th, 9 AM - 6:30 PM
$10, children under 12 are free

This is Long Island’s largest big rig truck show featuring over 200 heavy duty trucks, pick ups, haulers, custom made trucks, cars, and bikes. Kids will love the monster truck rides, facepainting, bounce houses, magic shows, and yummy food items. The trucks will be judged and prizes will be given out to the winners.

Long Island Cruzin’ For A Cure
Sears Auto Center, 195 North Broadway, Hicksville, NY 11801
Sunday, September 14th, 9 AM - 3 PM
$5, kids under 12 are free

Come out to show your support and help promote prostate cancer awareness. Over 600 vehicles will be exhibited with over 3,00 attendees expected. There will be a food court, games, vendors, and more.

2nd Annual Cruisin’ For Kids Sake Charity
Big Brother Big Sisters of Long Island, Levittown office, 70 Acorn Lane, Levittown, NY 11756
Saturday, September 20th, 9 AM
$25 registration

Hosted by Big Brothers Big Sisters in Levittown, get ready to cruise from Long Island to Bear Mountain in support of mentoring and making a difference.

Walks & Runs
Get active this September by participating in a local walk or run. The majority of runs are hosted for a good cause so you can feel good about helping towards the proceeds and maybe even make a few new exercise buddies while you do it.

The Color Vibe 5K
Eisenhower Park, 1899 Hempstead Turnpike, East Meadow, NY 11554
Saturday, September 6th, 9 AM

Don’t wear your favorite running gear to this run! Participants will be running along, untimed, as volunteers throw colored corn starch on the runners passing by. The party doesn’t stop there either. Afterwards a DJ will kick things off with even more color being thrown around.

Smith Point Bridge 5K Run for Literacy
Smith Point County Park, County Rd. 46, Shirley, NY 11967
Saturday, September 6th, 9 AM
$22 - $25

This race course crosses back and forth over the Smith Point Bridge with the finish line located on the beach pavilion. Proceeds support the community family literacy project and the reach out and read program at the Marilyn Shellabargar South Brookhaven Family Health Center.

Fit & Healthy Mamas 5K Run/Walk
Eisenhower Park, Hempstead Turnpike and Park Blvd., East Meadow, NY 11554
Saturday, September 13th, 8:30 AM
$25 - $30

Celebrate healthy living and exercise with this fun 5K. There will be tons of post race activities for both adults and kids.

Town of Huntington Triathlon
Crab Meadow Beach, 220 Waterside Ave., Northport, NY 11768
Sunday, September 14th
$65 - $150

Presented by Huntington Honda, this triathlon will include a 750-meter swim, 9.8-mile bike, 3.3-mile run. The race benefits Students for 60,000 and Northport Food Pantry.

Long Island Adventure Race
Veterans Memorial Park, Route 25, Calverton, NY 11933
Sunday, September 14th, 9 AM
$39 - $79

This isn’t just any race, this race involves running, obstacles, mud pits, and many more surprises. Anyone age 8 and up are welcome to participate.

Let’s Walk Let’s Talk
Long Beach Boardwalk, Long Beach, NY 11561
Sunday, September 21st, 10:30 AM

Don’t miss out on the, “Let’s Walk Let’s Talk” walk to benefit The Long Island Crisis Network. The Long Island Crisis Network provides free, 24/7 confidential services and programs to help Long Islanders get through the most critical times of their lives.

Wines and Canines Walk/Run
Baiting Hollow Farm Vineyard & Horse Rescue, 2114 Sound Ave., Baiting Hollow, NY 11933
Sunday, September 21st, 10 AM
$30, kids under 12 free

This leisurely walk/run is being held to benefit Kent Animal Shelter. There will be inexpensive canine vaccines and micro chipping, a raffle auction, caricatures, and food and wine for sale at the run.

Bideawee 5K Walk + Run
The East Quogue Village Green, East Quogue, NY 11942
Saturday, September 27th, 11 AM

This run, hosted by Bideawee a leading pet welfare agency, will help to raise funds to offset the cost of the life-altering veterinary care, behavioral training, food and shelter that Bideawee provides the animals in their adoption facility.

Bethpage Federal Credit Union Ocean to Sound Relay
Jones Beach State Park, 1000 Ocean Parkway, Wantagh, NY 11793
Sunday, September 28th, 8 AM
$40 per runner, $320 per team, $360 on race day

Get together a team of 8 of your fastest mates and sign up for this 50 mile relay race from Jones Beach to Oyster Bay. Each runner will be doing 5-7 miles each.

Step Out: Walk to STOP Diabetes
Jones Beach State Park, 1000 Ocean Parkway, Wantagh, NY 11793
Sunday, September 28th, 9 AM

Step Out: Walk to STOP Diabetes benefits the American Diabetes Association who help to prevent and cure diabetes and improve the lives of those affected by the disease. The run will also have a kids zone, live music, massages, and other entertainment.

More Super September Fun
Even with all of the festivals, fairs, races, car shows, and other events going on in September, there is still even more activities to do and fun to be had this month.

  • Apple Picking: Apples of all different colors and tastes are crisp and ripe for the taking at local Long Island farm stands and orchards.
  • Fall Foliage Viewing: Strap on a reliable pair of boots, or comfortable sneakers, as you take a stroll through nature and view all of the beautiful fall foliage.
  • Farmers Markets: Visit a farmers market to pick up some fresh, locally grown produce and support local farmers and businesses.
  • Hiking: The weather is perfect for a hiking adventure through the trails. Hike one of your favorite routes or discover a new one altogether.

Want to know about even more events and activities taking place this September? Well, voilà! Check out our Events Calendar for details on everything going on this month and our Things To Do section for activity ideas!

Photo by zirzuke via Free Images